Pyridine carboxamide derivatives and their use as pesticides

ABSTRACT

The invention relates to 3-pyridylcarboxamide derivatives of the formula (I): 
                         
wherein the various symbols are as defined in the description, compositions thereof, methods for controlling pests by applying same, and processes for their preparation.

CROSS-REFERENCE TO RELATED APPLICATIONS

This application is the U.S. national stage of International Appln. No.PCT/EP2003/004714, filed May 6, 2003, and claims priority under 35U.S.C. § 119(a)-(d) of European Patent Application No. 02010910.4, filedMay 16, 2002, said applications being incorporated by reference hereinin their entireties and relied upon.

The invention relates to 3-pyridylcarboxamide derivatives and their usefor the control of pests, in particular arthropods such as insects andacarids, and helminths (including nematodes); to compositions containingthem, and to processes and intermediates for their preparation.

The control of insects, nematodes or helminths with 3-pyridylcarboxamidecompounds has been described in many patents such as EP 580374, JP10101648, JP 10182625, WO 200109104, WO 200114340, JP 6321903, JP10195072 and JP 11180957.

However, the level of action and/or duration of action of theseprior-art compounds is not entirely satisfactory in all fields ofapplication, in particular against certain organisms or when lowconcentrations are applied.

Since modern pesticides must meet a wide range of demands, for exampleregarding level, duration and spectrum of action, use spectrum,toxicity, combination with other active substances, combination withformulation auxiliaries or synthesis, and since the occurrence ofresistances is possible, the development of such substances can never beregarded as concluded, and there is constantly a high demand for novelcompounds which are advantageous over the known compounds, at least asfar as some aspects are concerned.

It is an object of the present invention to provide compounds whichwiden the spectrum of the pesticides in various aspects.

The present invention provides a compound which is a3-pyridylcarboxamide derivative of formula (I):

wherein:

-   R¹ is —C(═U)NR³R⁴ or —C(═V)OR^(3a);-   R² is H, (C₁-C₆)alkyl or R³;-   R³ is R⁵, OH or NH₂; or is (C₁-C₆)alkyl substituted by one or more    R⁶ groups;-   or R² and R³ together with the interconnecting atoms form a    heterocyclic ring selected from (A), (B), (C), (D) and (E);

-   R^(3a) is (C₃-C₈)cycloalkyl or (C₃-C₈)cycloalkyl-(C₁-C₆)alkyl, which    cycloalkyl groups are unsubstituted or substituted by one or more    (C₁-C₆)alkyl, (C₁-C₆)haloalkyl or R⁶ groups; or is (C₁-C₆)alkyl,    (C₃-C₆)alkenyl or (C₃-C₆)alkynyl which last three mentioned groups    are substituted by one or more R⁶ groups; or is (C₁-C₆)alkylamino;-   or is NH(CHR¹⁴)_(s)aryl which aryl group is unsubstituted or    substituted by one or more R⁶ groups;-   R⁴ is H or R⁵; or is (C₁-C₆)alkyl unsubstituted or substituted by    one or more R⁶ groups;-   or R³ and R⁴ together with the adjacent N atom form a 3 to    8-membered unsaturated, partially saturated or saturated    heterocyclic ring which optionally contains up to three additional    N, O or S atoms and which ring is unsubstituted or substituted by    one or more R⁶ or R^(14a) groups (preferred examples of such ring    systems include pyrrolidin-1-yl, pyrrolin-1-yl, piperidin-1-yl,    morpholin-1-yl (or its N-oxide), thiomorpholin-1-yl (or its S-oxide    or S,S-dioxide), 4,5-dihydropyrazol-1-yl or pyrazol-1-yl);-   R⁵ is (C₃-C₆)alkenyl, (C₃-C₆)alkynyl, (C₃-C₈)cycloalkyl,    (C₁-C₆)alkoxy, (C₃-C₆)alkenyloxy, (C₃-C₆)alkynyloxy,    (C₁-C₆)alkylamino, di-(C₁-C₆)alkylamino, CO(C₁-C₆)alkyl,    NHCO(C₁-C₆)alkyl, NHSO₂(C₁-C₆)alkyl or SO₂(C₁-C₆)alkyl which last 12    mentioned groups are unsubstituted or substituted by one or more R⁶    groups; or is (C₃-C₈)cycloalkyl-(C₁-C₆)alkyl which cycloalkyl group    is unsubstituted or substituted by one or more R⁶ groups; or is    NH(CHR¹⁴)_(s)aryl, —(CR¹⁵R¹⁶)_(p)aryl, O(R¹⁵R¹⁶)_(r)aryl, NHCOaryl,    CO(CH₂)_(t)aryl, NHSO₂aryl, SO₂(CH₂)_(u)aryl or N═C(aryl)₂,    —(CR¹⁵R¹⁶)_(p)heterocyclyl or O(R¹⁵R¹⁶)_(r)heterocyclyl, which last    ten mentioned aryl or heterocyclyl groups are unsubstituted or    substituted by one or more R¹⁷ groups; or is    O(CR¹⁵R¹⁶)_(p)(C₃-C₈)cycloalkyl or N═C[(C₁-C₆)alkyl]₂;-   R⁶ is halogen, (C₁-C₆)alkoxy, (C₁-C₆)haloalkoxy, S(O)_(n)R^(14a),    CN, CO₂(C₁-C₆)alkyl, CO₂H, NO₂, OH, amino, (C₁-C₆)alkylamino,    di-(C₁-C₆)alkylamino, carbamoyl, (C₁-C₆)-alkylcarbamoyl,    di-(C₁-C₆)-alkylcarbamoyl or CH[O(C₁-C₆)alkyl]₂; or is phenoxy    unsubstituted or substituted by one or more R^(14a) or halogen    groups;-   R¹⁷ is R⁶, R^(14a) or CH₂OH;-   U is S, O or NR¹⁸;-   V is O or S;-   W is (CHR¹⁹)_(q), CO or NR²⁰;-   X is CR²¹ or N;-   Y is CR²² or N;-   Z is O, CO or NR²³;-   R⁷, R⁸, R⁹, R¹², R¹⁹, R²¹ and R²² are each independently H; or    (C₁-C₆)alkyl, (C₂-C₆)alkenyl, (C₂-C₆)alkynyl, (C₃-C₈)cycloalkyl,    (C₁-C₆)alkoxy, (C₂-C₆)alkenyloxy or (C₂-C₆)alkynyloxy, which last    seven mentioned groups are unsubstituted or substituted by one or    more R⁶ groups; or is —(CH₂)_(p)aryl or heterocyclyl, which aryl or    heterocyclyl groups are unsubstituted or substituted by one or more    R⁶ groups; or (C₃-C₈)cycloalkyl-(C₁-C₆)alkyl which cycloalkyl group    is unsubstituted or substituted by one or more R⁶ groups;-   or R⁷ and R⁸ together with the attached carbon atom may represent    C═O;-   R¹⁰, R²⁰ and R²³ are each independently H; or (C₁-C₆)alkyl,    (C₃-C₆)alkenyl, (C₃-C₆)alkynyl or (C₃-C₈)cycloalkyl, which last four    mentioned groups are unsubstituted or substituted by one or more R⁶    groups; or is (C₃-C₈)cycloalkyl-(C₁-C₆)alkyl which cycloalkyl group    is unsubstituted or substituted by one or more R⁶ groups; or is    —(CH₂)_(p)aryl or heterocyclyl which aryl or heterocyclyl groups are    unsubstituted or substituted by one or more R⁶ groups;-   R¹¹ is R⁷, halogen, CN, CO₂(C₁-C₆)alkyl, NO₂ or S(O)_(n)R¹⁴; or is    (C₁-C₆)alkylamino or di-(C₁-C₆)alkylamino, which groups are    unsubstituted or substituted by one or more R⁶ groups;-   R¹³ is R⁷ or OH;-   R¹⁴, R¹⁵ and R¹⁶ are each independently H, (C₁-C₆)alkyl or    (C₁-C₆)haloalkyl;-   R^(14a) is (C₁-C₆)alkyl or (C₁-C₆)haloalkyl;-   R¹⁸ is R⁷ or OH; or is (C₁-C₆)alkylamino or di-(C₁-C₆)alkylamino,    which groups are unsubstituted or substituted by one or more R⁶    groups;-   m is zero or one;-   n, p, r, s, t and u are each independently zero, one or two;-   q is one, two or three; and each heterocyclyl in the above mentioned    radicals is independently a heterocyclic radical having 3 to 7 ring    atoms and 1 to 4 hetero atoms selected from N, O and S;-   or a pesticidally acceptable salt thereof;-   with the exclusion of the compound wherein R¹ is —C(═U)NR³R⁴; U is    O; R² is H; m is zero; R⁴ is H and R³ is 2,4-dichlorophenyl.

These compounds possess valuable pesticidal properties.

The invention also encompasses any stereoisomer, enantiomer or geometricisomer, and mixtures thereof.

By the term “pesticidally acceptable salts” is meant salts the cationsor anions of which are known and accepted in the art for the formationof salts for pesticidal use. Suitable salts with bases, e.g. formed bycompounds of formula (I) containing a carboxy or OH group, includealkali metal (e.g. sodium and potassium), alkaline earth metal (e.g.calcium and magnesium), ammonium and amine (e.g. diethanolamine,triethanolamine, octylamine, morpholine and dioctylmethylamine) salts.Suitable acid addition salts, e.g. formed by compounds of formula (I)containing an amino group, include salts with inorganic acids, forexample hydrochlorides, sulphates, phosphates and nitrates and saltswith organic acids for example acetic acid.

The term pests means arthropod pests (including insects and acarids),and helminths (including nematodes).

In the present patent specification, including the accompanying claims,the aforementioned substituents have the following meanings:

-   halogen atom means fluorine, chlorine, bromine or iodine;-   alkyl groups and portions thereof (unless otherwise defined) may be    straight- or branched-chain;-   cycloalkyl groups preferably have from three to six carbon atoms in    the ring and are optionally substituted by halogen or alkyl.

The haloalkyl and haloalkoxy groups can bear one or more halogen atoms;preferred groups of this type include —CF₃ and —OCF₃.

The term “halo” before the name of a radical means that this radical ispartially or completely halogenated, that is to say, substituted by F,Cl, Br, or I, in any combination, preferably by F or Cl.

The expression “(C₁-C₆)-alkyl” is to be understood as meaning anunbranched or branched hydrocarbon radical having 1, 2, 3, 4, 5 or 6carbon atoms, such as, for example a methyl, ethyl, propyl, isopropyl,1-butyl, 2-butyl, 2-methylpropyl or tert-butyl radical.

“(C₁-C₆)-Haloalkyl” is to be understood as meaning an alkyl groupmentioned under the expression “(C₁-C₆)-alkyl” in which one or morehydrogen atoms are replaced by the same number of identical or differenthalogen atoms, preferably by chlorine or fluorine, such as thetrifluoromethyl, the 1-fluoroethyl, the 2,2,2-trifluoroethyl, thechloromethyl, fluoromethyl, the difluoromethyl or the1,1,2,2-tetrafluoroethyl group.

“(C₁-C₆)-Alkoxy” is to be understood as meaning an alkoxy group whosehydrocarbon radical has the meaning given under the expression“(C₁-C₆)-alkyl”.

The terms “alkenyl” and “alkynyl” with a range of carbon atoms stated asprefix denote a straight-chain or branched hydrocarbon radical having anumber of carbon atoms which corresponds to this stated range and whichcontains at least one multiple bond which can be located in any positionof the respective unsaturated radical. “(C₂-C₆)-Alkenyl” accordinglydenotes, for example, the vinyl, allyl, 2-methyl-2-propenyl, 2-butenyl,pentenyl, 2-methylpentenyl or the hexenyl group. “(C₂-C₆)-Alkynyl”denotes, for example, the ethynyl, propargyl, 2-methyl-2-propynyl;2-butynyl; 2-pentynyl or the 2-hexynyl group.

“(C₃-C₈)-Cycloalkyl” denotes monocyclic alkyl radicals, such as thecyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl orcyclooctyl radical, and denotes bicyclic alkyl radicals, such as thenorbornyl radical.

The expression “(C₃-C₈)-cycloalkyl-(C₁-C₆)-alkyl” is to be understood asmeaning, for example the cyclopropylmethyl, cyclopentylmethyl,cyclohexylmethyl, cyclohexylethyl, cyclohexylbutyl, 1-methylcyclopropyl,1-methylcyclopentyl, 1-methylcyclohexyl, 3-hexylcyclobutyl or the4-tert-butylcyclohexyl radical.

“(C₁-C₆)-Alkylamino” denotes a nitrogen atom which is substituted by analkyl radical of the above definition. “Di-(C₁-C₆)-alkylamino” denotes anitrogen atom which is substituted by two alkyl radical of the abovedefinition.

The expression “(C₁-C₆)-alkylcarbamoyl” denotes a carbamoyl group havingone hydrocarbon radical which has the meaning given under the expression“(C₁-C₆)-alkyl”; and “di-(C₁-C₆)-alkylcarbamoyl” denotes a carbamoylgroup having two hydrocarbon radicals which can be identical ordifferent.

The expression “aryl” is to be understood as meaning a carbocyclic, i.e.constructed of carbon atoms, aromatic radical having preferably 6 to 14,in particular 6 to 12, carbon atoms, such as, for example, phenyl,naphthyl or biphenylyl, preferably phenyl.

The expression “heterocyclyl” preferably denotes a cyclic radical whichcan be completely saturated, partially unsaturated or completelyunsaturated and which contains in the ring one or more identical ordifferent atoms selected from the group consisting of nitrogen, sulfurand oxygen, where, however, two oxygen atoms may not be directlyadjacent and at least one carbon atom has to be present in the ring,such as, for example, a thiophene, furan, pyrrole, thiazole, oxazole,imidazole, isothiazole, isoxazole, pyrazole, 1,3,4-oxadiazole,1,3,4-thiadiazole, 1,3,4-triazole, 1,2,4-oxadiazole, 1,2,4-thiadiazole,1,2,4-triazole, 1,2,3-triazole, 1,2,3,4-tetrazole, benzo[b]thiophene,benzo[b]furan, indole, benzo[c]thiophene, benzo[c]furan, isoindole,benzoxazole, benzothiazole, benzimidazole, benzisoxazole,benzisothiazole, benzopyrazole, benzothiadiazole, benzotriazole,dibenzofuran, dibenzothiophene, carbazole, pyridine, pyrazine,pyrimidine, pyridazine, 1,3,5-triazine, 1,2,4-triazine,1,2,4,5-tetrazine, quinoline, isoquinoline, quinoxaline, quinazoline,cinnoline, 1,8-naphthyridine, 1,5-naphthyridine, 1,6-naphthyridine,1,7-naphthyridine, phthalazine, pyridopyrimidine, purine, pteridine,4H-quinolizine, piperidine, pyrrolidine, oxazoline, tetrahydrofuran,tetrahydropyran, isoxazolidine, thiazolidine, oxirane or oxetaneradical.

Heterocyclyl preferably denotes a saturated, partially saturated oraromatic ring system having 3 to 7 ring members and 1 to 4 heteroatomsselected from the group consisting of O, S and N, where at least onecarbon atom has to be present in the ring.

More preferably, heterocyclyl denotes a pyridine, pyrimidine,(1,2,4)-oxadiazole, (1,3,4)-oxadiazole, (1,3,4)-thiadiazole,(1,2,4)-thiadiazole, pyrrole, furan, thiophene, oxazole, thiazole,benzothiazole, imidazole, pyrazole, isoxazole, 1,2,4-triazole,tetrazole, pyrimidine, pyrazine, pyridazine, oxazoline, thiazoline,tetrahydrofuran, tetrahydropyran, morpholine, piperidine, piperazine,pyrroline, pyrrolidine, oxazolidine or thiazolidine radical(particularly a pyridine, pyrimidine, (1,2,4)-oxadiazole,(1,3,4)-oxadiazole, (1,3,4)-thiadiazole, 1,2,4-thiadiazole, thiazole,pyrazole, pyrrole, isoxazole, benzothiazole, 1,2,4-triazole, pyrazine,pyridazine, oxirane or oxetane radical).

Preferred substituents for the various aliphatic, aromatic andheterocyclic ring systems include halogen, nitro, cyano, (C₁-C₄)-alkyl,(C₃-C₆)-cycloalkyl, (C₁-C₄)-alkoxy, (C₁-C₄)-alkylthio,(C₁-C₄)-alkylsulfinyl, (C₁-C₄)-alkylsulfonyl, phenyl, benzyl or phenoxy,where in the alkyl radicals and the radicals derived therefrom one ormore—and in the case of fluorine up to the maximum number of—hydrogenatoms can be replaced by halogen, preferably chlorine or fluorine.

More preferred substituents include halogen, nitro, cyano,(C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, (C₃-C₆)-cycloalkyl, (C₁-C₄)-alkoxy,(C₁-C₄)-haloalkoxy, (C₁-C₄)-alkylthio or (C₁-C₄)-haloalkylthio.

Most preferred substituents include halogen, nitro, cyano,(C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, (C₁-C₄)-alkoxy, (C₁-C₄)-haloalkoxy,(C₁-C₄)-alkylthio or (C₁-C₄)-haloalkylthio.

It is to be generally understood, unless otherwise stated, that the term“unsubstituted or substituted by one or more groups” or “unsubstitutedor substituted by one or more groups selected from” means that suchgroups (or preferred groups) may be the same or different.

-   R¹ is preferably —C(═U)NR³R⁴;-   R² is preferably H or R³ (more preferably R² is H);-   R³ is preferably R⁵ or OH; or is (C₁-C₆)alkyl substituted by one or    more R⁶ groups;-   or preferably R² and R³ together with the interconnecting atoms form    a heterocyclic ring selected from (A) and (C):

-   R⁴ is preferably H or R⁵, or is (C₁-C₆)alkyl unsubstituted or    substituted by one or more R⁶ groups;-   or R³ and R⁴ together with the adjacent N atom may form a 3 to    8-membered unsaturated, partially saturated or saturated    heterocyclic ring which optionally contains up to three additional    N, O or S atoms and which ring is unsubstituted or substituted by    one or more R⁶ or R^(14a) groups (particularly preferred examples of    such ring systems include pyrrolidin-1-yl, piperidin-1-yl,    morpholin-1-yl, thiomorpholin-1-yl or its S-oxide or S,S-dioxide);-   R⁵ is preferably (C₃-C₆)alkenyl, (C₃-C₆)alkynyl, (C₃-C₈)cycloalkyl,    (C₃-C₈)cycloalkyl-(C₁-C₆)alkyl, (C₁-C₆)alkoxy, (C₃-C₆)alkenyloxy,    (C₃-C₆)alkynyloxy or O(CR¹⁵R¹⁶)_(p)(C₃-C₈)cycloalkyl; or is    —(CR¹⁵R¹⁶)_(p)phenyl, —(CR¹⁵R¹⁶)_(p)heterocyclyl,    O(CR¹⁵R¹⁶)_(r)phenyl or O(CR¹⁵R¹⁶)_(r)heterocyclyl, which last four    mentioned phenyl or heterocyclyl groups are unsubstituted or    substituted by one or more R¹⁷ groups; (more preferably R⁵ is    (C₃-C₆)alkenyl, (C₃-C₆)alkynyl, (C₁-C₆)alkoxy, (C₃-C₆)alkenyloxy,    (C₃-C₆)alkynyloxy or O(CR¹⁵R¹⁶)_(p)(C₃-C₈)cycloalkyl; or is    —(CR¹⁵R¹⁶)_(p)phenyl, —(CR¹⁵R¹⁶)_(p)heterocyclyl,    O(CR¹⁵R¹⁶)_(r)phenyl or O(CR¹⁵R¹⁶)_(r)heterocyclyl, which last four    mentioned phenyl or heterocyclyl groups are unsubstituted or    substituted by one or more R¹⁷ groups);-   R⁶ is preferably halogen, (C₁-C₆)alkoxy, (C₁-C₆)haloalkoxy,    S(O)_(n)R^(14a), CN, NO₂ or OH; (more preferably R⁶ is halogen or    CN);-   R¹⁷ is preferably R⁶, R^(14a) or CH₂OH;-   U is preferably S or O;-   W is preferably (CHR¹⁹)_(q) or CO;-   Z is preferably O;-   R⁷, R⁸, R⁹, R¹⁰ and R¹⁹ are each preferably H; or (C₁-C₆)alkyl    unsubstituted or substituted by one or more R⁶ groups;-   or R⁷ and R⁸ together with the attached carbon atom represent C═O;-   R¹⁴, R¹⁵ and R¹⁶ are each preferably H or (C₁-C₆)alkyl;-   R^(14a) is preferably (C₁-C₆)alkyl or (C₁-C₆)haloalkyl;-   m is preferably zero;-   n, r, s, t and u are preferably zero or one;-   q is preferably one; and-   heterocyclyl preferably denotes a pyridine, pyrimidine,    (1,2,4)-oxadiazole, (1,3,4)-oxadiazole, (1,2,4)-thiadiazole,    (1,3,4)-thiadiazole, benzothiazole, pyrrole, furan, thiophene,    oxazole, thiazole, imidazole, pyrazole, isoxazole, 1,2,4-triazole,    tetrazole, pyrimidine, pyrazine, pyridazine, oxazoline, thiazoline,    tetrahydrofuran, tetrahydropyran, morpholine, piperidine,    piperazine, pyrroline, pyrrolidine, oxazolidine, thiazolidine,    oxirane or oxetane radical.

A preferred class of compounds of formula (I) are those in which:

-   R¹ is —C(═U)NR³R⁴ or —C(═V)OR^(3a);-   R^(3a) is (C₃-C₈)cycloalkyl or (C₃-C₈)cycloalkyl-(C₁-C₆)alkyl, which    cycloalkyl groups are unsubstituted or substituted by one or more    (C₁-C₆)alkyl, (C₁-C₆)haloalkyl or R⁶ groups; or is (C₁-C₆)alkyl,    (C₃-C₆)alkenyl or (C₃-C₆)alkynyl which last three mentioned groups    are substituted by one or more R^(6a) groups; or is    (C₁-C₆)alkylamino; or is NH(CHR¹⁴)_(s)aryl which aryl group is    unsubstituted or substituted by one or more R⁶ groups;-   R^(6a) is (C₁-C₆)alkoxy, (C₁-C₆)haloalkoxy, S(O)_(n)R^(14a),    CO₂(C₁-C₆)alkyl, CO₂H, amino, (C₀-C₆)alkylamino, carbamoyl,    (C₁-C₆)-alkylcarbamoyl, di-(C₁-C₆)-alkylcarbamoyl or    CH[O(C₁-C₆)alkyl]₂; or is phenoxy unsubstituted or substituted by    one or more R^(14a) or halogen groups;-   and the other values are as defined in formula (I).

A further preferred class of compounds of formula (I) are those inwhich:

-   R¹is —C(═U) NR³R⁴;-   R² is H;-   R³ is R⁵ or OH; or is (C₁-C₆)alkyl substituted by one or more R⁶    groups;-   or R² and R³ together with the interconnecting atoms may form a    heterocyclic ring selected from (A) and (C):

-   R⁴ is H or R⁵, or is (C₁-C₆)alkyl unsubstituted or substituted by    one or more R⁶ groups;-   or R³ and R⁴ together with the adjacent N atom may form a    pyrrolidin-1-yl, piperidin-1-yl, morpholin-1-yl or    thiomorpholin-1-yl (or its S-oxide or S,S-dioxide) ring;-   R⁵ is (C₃-C₆)alkenyl, (C₃-C₆)alkynyl, (C₃-C₈)cycloalkyl,    (C₃-C₈)cycloalkyl-(C₁-C₆)alkyl, (C₁-C₆)alkoxy, (C₃-C₆)alkenyloxy,    (C₃-C₆)alkynyloxy or O(CR¹⁵R¹⁶)_(p)(C₃-C₈)cycloalkyl;-   or —(CR¹⁵R¹⁶)_(p)phenyl, —(CR¹⁵R¹⁶)_(p)heterocyclyl,    O(CR¹⁵R¹⁶)_(r)phenyl or O(CR¹⁵R¹⁶)_(r)heterocyclyl, which last four    mentioned phenyl or heterocyclyl groups are unsubstituted or    substituted by one or more R¹⁷ groups;-   R⁶ is halogen, (C₁-C₆)alkoxy, (C₁-C₆)haloalkoxy, S(O)_(n)R^(14a),    CN, NO₂ or OH;-   R¹⁷ is R⁶, R^(14a) or CH₂OH;-   U is S or O;-   W is (CHR¹⁹)_(q) or CO;-   Z is O;-   R⁷, R⁸, R⁹, R¹⁰ and R¹⁹ are each H; or (C₁-C₆)alkyl unsubstituted or    substituted by one or more R⁶ groups;-   or R⁷ and R⁸ together with the attached carbon atom represent C═O;-   R¹⁴, R¹⁵ and R¹⁶ are each H or (C₁-C₆)alkyl;-   R^(14a) is (C₁-C₆)alkyl or (C₁-C₆)haloalkyl;-   m is zero;-   n, r, s, t and u are zero, one or two;-   q is one; and wherein heterocyclyl denotes a pyridine, pyrimidine,    (1,2,4)-oxadiazole, (1,3,4)-oxadiazole, (1,2,4)-thiadiazole,    (1,3,4)-thiadiazole, pyrrole, furan, thiophene, oxazole, thiazole,    benzothiazole, imidazole, pyrazole, isoxazole, 1,2,4-triazole,    tetrazole, pyrazine, pyridazine, oxazoline, thiazoline,    tetrahydrofuran, tetrahydropyran, morpholine, piperidine,    piperazine, pyrroline, pyrrolidine, oxazolidine, thiazolidine,    oxirane or oxetane radical.

A further preferred class of compounds of formula (I) are those inwhich:

-   R¹ is —C(═U)NR³R⁴;-   R² is H;-   U is O or S;-   R³ is (C₁-C₆)haloalkyl, (C₃-C₆)alkenyl, (C₃-C₆)alkynyl,    (C₃-C₈)cycloalkyl, (C₃-C₈)cycloalkyl(C₁-C₆)alkyl, (C₃-C₆)alkenyloxy,    (C₃-C₆)alkynyloxy, NH₂, (C₁-C₆)alkylamino, OH, Ophenyl, pyrimidyl,    benzothiazolyl, thiazolyl, thiadiazolyl, —(CH₂)₂pyrrolidin-1-yl,    NHSO₂phenyl, NHCO(C₁-C₆)alkyl, NHSO₂(C₁-C₆)alkyl, NHCOphenyl or    N═C(phenyl)₂; or is pyridyl unsubstituted or substituted by one or    more groups selected from halogen, (C₁-C₆)alkyl, (C₁-C₆)alkoxy, CN    and NO₂; or is OCH₂phenyl which phenyl is unsubstituted or    substituted by one or more groups selected from halogen,    (C₁-C₆)alkyl, CN and NO₂; or is (C₁-C₆)alkoxy unsubstituted or    substituted by a CO₂(C₁-C₆)alkyl group;-   or is —(CHR¹⁵)_(p)phenyl wherein p is 0, 1 or 2, R¹⁵ is H or    (C₁-C₆)alkyl, and phenyl is unsubstituted or substituted by one or    more groups selected from halogen, (C₁-C₆)alkyl, (C₁-C₆)haloalkyl,    (C₁-C₆)alkoxy, (C₁-C₆)haloalkoxy, CN, NO₂, OH, CH₂OH,    CO₂(C₁-C₆)alkyl and phenoxy which phenoxy is unsubstituted or    substituted by one or more groups selected from halogen and    (C₁-C₆)haloalkyl;-   or is (C₁-C₆)alkyl unsubstituted or substituted by one or more    groups selected from (C₁-C₆)alkoxy, CN, OH, CO₂(C₁-C₆)alkyl and    CH[O(C₁-C₆)alkyl]₂;-   or is NH(CH₂)_(s)phenyl wherein s is zero or 1;-   R⁴ is H, (C₁-C₆)alkyl, (C₃-C₆)alkenyl, (C₃-C₆)alkynyl,    (C₃-C₈)cycloalkyl, —(CH₂)_(p)phenyl wherein p is 0 or 1, or    N═C[(C₁-C₆)alkyl]₂;-   or R³ and R⁴ together with the adjacent N atom may form a    pyrrolidin-1-yl, piperidin-1-yl, morpholin-1-yl, thiomorpholin-1-yl    which groups are unsubstituted or substituted by one or more groups    selected from halogen, (C₁-C₆)alkyl and OH; or form a    4,5-dihydropyrazol-1-yl ring; and-   m is zero.

A further preferred class of compounds of formula (I) are those inwhich:

-   R¹ is —C(═U)NR³R⁴;-   U is O;-   R² is (C₁-C₆)alkyl, (C₃-C₆)alkenyl, (C₃-C₆)alkynyl or CH₂phenyl; or    is (C₁-C₆)alkyl substituted by CO₂(C₁-C₆)alkyl or CH[O(C₁-C₆)alky]₂;-   R³ is (C₃-C₆)alkenyloxy, (C₃-C₆)alkynyloxy, CH₂phenyl or OCH₂phenyl;    or is (C₁-C₆)alkoxy unsubstituted or substituted by one or two    CO₂(C₁-C₆)alkyl groups;-   R⁴ is H or (C₁-C₆)alkyl; and-   m is zero.

A further preferred class of compounds of formula (I) are those inwhich:

-   R¹ is —C(═U)NR³R⁴;-   R² and R³ together with the interconnecting atoms form a    heterocyclic ring selected from (A) and (C):

wherein U is O or S;

-   and in (A):-   W is CH₂, CO or CHR¹⁹ wherein R¹⁹ is H, (C₁-C₆)alkyl or phenyl;-   R⁴ is H, (C₁-C₆)alkyl, phenyl, CH₂phenyl or OCH₂phenyl;-   R⁷ is H, (C₁-C₆)alkyl, (C₁-C₆)alkoxy or phenyl; and-   R⁸ is H or (C₁-C₆)alkyl;-   and in (C):-   Z is O;-   R⁴ is (C₁-C₆)alkyl, (C₃-C₈)cycloalkyl or CH₂phenyl; and-   R⁹ and R¹⁰ are each H; and-   m is zero.

A further preferred class of compounds of formula (I) are those inwhich:

-   R¹ is —C(═U)NR³R⁴;-   wherein U is NR¹⁸;-   R² is H;-   R³ is (C₁-C₆)alkyl, (C₃-C₆)alkenyl, (C₃-C₈)cycloalkyl; or is    (C₁-C₆)alkyl substituted by one or two (C₁-C₆)alkoxy or    CH[O(C₁-C₆)alkyl]₂ groups;-   R⁴ and R¹⁸ are each the same or different H or (C₁-C₆)alkyl;-   or R³ and R⁴ together with the adjacent N atom form a morpholin-1-yl    or pyrazol-1-yl ring; and-   m is zero.

A further preferred class of compounds of formula (I) are those inwhich:

-   R¹ is —C(═V)OR^(3a);-   wherein V is O or S;-   R² is H, (C₃-C₈)cycloalkyl-(C₁-C₆)alkyl, NHCH₂phenyl; or is    (C₁-C₆)alkyl substituted by a group selected from (C₁-C₆)alkoxy, CN,    OH and S(O)_(n)R^(14a);-   R^(3a) is (C₃-C₈)cycloalkyl or (C₃-C₈)cycloalkyl-(C₁-C₆)alkyl, which    cycloalkyl groups are unsubstituted or substituted by one or more R⁶    groups; or is (C₁-C₆)alkyl, (C₃-C₆)alkenyl or (C₃-C₆)alkynyl which    last three mentioned groups are substituted by one or more R⁶    groups; or is (C₁-C₆)alkylamino; or is NH(CHR¹⁴)_(s)aryl which aryl    group is unsubstituted or substituted by one or more R⁶ groups; and-   m is zero.

A more preferred class of compounds of formula (I) are those in which:

-   R¹ is —C(═U)NR³R⁴;-   R² is H;-   U is O or S;-   R³ is (C₁-C₆)alkoxy, C₁-C₆)haloalkoxy, (C₃-C₆)alkenyloxy,    (C₃-C₆)alkynyloxy, CH₂phenyl or OCH₂phenyl, phenyl or 2-pyridyl    which last four mentioned phenyl or pyridyl groups are unsubstituted    or substituted by one or more groups selected from halogen,    (C₁-C₆)alkyl, (C₁-C₆)alkoxy, CN and NO2;-   R⁴ is H, (C₁-C₆)alkyl, (C₃-C₆)alkenyl, (C₃-C₆)alkynyl or CH₂phenyl;    and-   m is zero.

A further more preferred class of compounds of formula (I) are those inwhich:

-   R¹ is —C(═U)NR³R⁴;-   R² is H;-   U is O;-   R³ is (C₁-C₆)alkoxy;-   R⁴ is (C₁-C₆)alkyl; and-   m is zero.

The compounds of general formula (I) can be prepared by the applicationor adaptation of known methods (i.e. methods heretofore used ordescribed in the chemical literature.

In the following description of processes when symbols appearing informulae are not specifically defined, it is understood that they are“as defined above” in accordance with the first definition of eachsymbol in the specification.

According to a feature of the invention compounds of formula (I) whereinR¹ is —C(═U)NR³R⁴, m is zero, and R², U, R³ and R⁴ are as defined above;or R² and R³ together with the interconnecting atoms form a heterocyclicring selected from (A), (B), (C), (D) and (E);

wherein R⁴, R⁷, R⁸, R⁹, R¹⁰, R¹¹, R¹², R¹³, W, X, Y and Z are as definedabove, may be prepared by the reaction of a compound of formula (II):

wherein L is a leaving group, generally halogen and preferably chlorine,with a compound of formula (III):HNR²—C(═U)NR³R⁴  (III)wherein R², U, R³ and R⁴ are as defined above, or with a compound offormula (IV), (V), (VI); (VII) or (VIII):

wherein R⁴, R⁷, R⁸, R⁹, R¹⁰, R¹¹, R¹², R¹³, W, X, Y and Z are as definedabove. The reaction is generally performed in the presence of an organicbase such as a tertiary amine for example triethylamine, or pyridine, oran inorganic base such as an alkali metal carbonate, for examplepotassium carbonate, or an alkali metal alkoxide such as sodiumethoxide, or sodium hydride, in a solvent such as dioxan,tetrahydrofuran or N,N-dimethylformamide, at a temperature of from 0° to100° C. (preferably 0° to 50° C.).

According to a further feature of the present invention compounds offormula (I) wherein R¹ is —C(═U)NR³R⁴, m is zero, R² is H, U is O, andR³ and R⁴ are as defined above, may be prepared by the reaction of acompound of formula (IX):

with oxalyl chloride or triphosgene, in an inert solvent such asdichloroethane at a temperature of from 0° C. to the reflux temperatureof the solvent, followed by removal of the solvent to give thecorresponding acylisocyanate intermediate which is generally notisolated, and which is directly reacted with an amine of formula (X):HNR³R⁴  (X)

-   wherein R³ and R⁴ are as defined above. The reaction is generally    performed in an inert solvent such as dichloroethane or    tetrahydrofuran at a temperature of from 0° to 60° C.

According to a further feature of the present invention compounds offormula (I) wherein R¹ is —C(═V)OR^(3a), m is zero, R² is H, V is O, andR^(3a) is as defined above, may be prepared by the reaction of acompound of formula (IX) as defined above, with oxalyl chloride to givean acylisocyanate intermediate above which is generally not isolated,and which is directly reacted with an alcohol of formula (XI):HOR^(3a)  (XI)wherein R³ is as defined above. The reaction is generally performed inan inert solvent such as dichloroethane or tetrahydrofuran at atemperature of from 0° to 60° C.

According to a further feature of the present invention compounds offormula (I) wherein R¹ is —C(═U)NR³R⁴, m is zero, R² is H, U is O or S,and R³ and R⁴ are as defined above, may be prepared by the reaction of acompound of formula (XII).

wherein U is O or S, with a compound of formula (X) as defined above.The reaction is generally performed in an inert solvent such asdichloroethane or tetrahydrofuran at a temperature of from 0° to 60° C.

According to a further feature of the present invention compounds offormula (I) wherein R¹ is —C(═V)OR^(3a), m is zero, R² is H, V is O orS, and R^(3a) is as defined above, may be prepared by the reaction of acompound of formula (XIII).

wherein V is O or S, with a compound of formula (XI) as defined above.The reaction is generally performed in an inert solvent such asdichloroethane or tetrahydrofuran at a temperature of from 0° to 60° C.

According to a further feature of the present invention compounds offormula (i) wherein R¹ is —C(═U)NR³R⁴, m is zero, R² is H, R⁴ is H, U isO or S, and R³ is as defined above, may be prepared by the reaction of acompound of formula (IX) as defined above, with a strong base such assodium hydride to form the corresponding salt, which is then reactedwith a compound of formula (XIV):R³N═C═U  (XIV)wherein R³ is as defined above. The reaction is generally performed inan inert solvent such as N,N-dimethylformamide at a temperature of from0° to 60° C.

According to a further feature of the present invention compounds offormula (I) wherein R¹ is —C(═U)NR³R⁴ or —C(═V)OR^(3a), m is zero, R² isH, U and V are each S, and R³, R^(3a) and R⁴ are as defined above, maybe prepared in a 1-pot process by the reaction of4-trifluoromethylnicotinic acid with a suitable halogenating agent,preferably oxalyl chloride, in a solvent such as dichloroethane,optionally in the presence of N,N-dimethylformamide, at a temperature offrom 0° C. to the reflux temperature of the solvent, to give thecorresponding acid chloride, followed by removal of the solvent, andreaction with an alkali metal thiocyanate or ammonium thiocyanate or atetraalkylammonium thiocyanate for example tetrabutylammoniumthiocyanate, generally in the presence of a base, such as an alkalimetal carbonate for example potassium carbonate, in an inert solventsuch as toluene or acetone, at a temperature of from 0° to 60° C., togive 4-trifluoromethyl-3-pyridylcarbonyl isothiocyanate, followed byreaction with an amine of formula (X) above or an alcohol of formula(XI) above, at a temperature of from 0° to 60° C.

According to a further feature of the invention compounds of formula (I)wherein R¹ is —C(═U)NR³R⁴, m is zero, U, R³ and R⁴ are as defined above,and R² is (C₁-C₆)alkyl, (C₃-C₆)alkenyl, (C₃-C₆)alkynyl,(C₃-C₈)cycloalkyl or (C₃-C₈)cycloalkyl-(C₁-C₆)alkyl which groups areunsubstituted or substituted by one or more R⁶ groups; or is—(CR¹⁵R¹⁶)_(p)aryl or —(CR¹⁵R¹⁶)_(p)heterocyclyl, which aryl orheterocyclyl groups are optionally substituted by R¹⁷; wherein R⁶, R¹⁵,R¹⁶ and R¹⁷ are as defined above, may be prepared by the reaction of thecorresponding compound of formula (I) wherein R² is H, using analkylatig agent of formula (XV):R²-L¹  (XV)wherein L¹ is a leaving group generally halogen and preferably chlorine.The reaction is generally performed in the presence of an organic basesuch as a tertiary amine for example triethylamine, or pyridine, or aninorganic base such as an alkali metal carbonate, for example potassiumcarbonate, or an alkali metal alkoxide such as sodium ethoxide, orsodium hydride, in a solvent such as dioxan, tetrahydrofuran orN,N-dimethylformamide, at a temperature of from 0° to 100° C.(preferably 0° to 50° C.).

According to a further feature of the invention compounds of formula (I)wherein R¹, and R² are as defined above, and m is 1 may be prepared byoxidising a corresponding compound in which m is 0. The oxidation isgenerally performed using hydrogen peroxide in a solvent such as aceticacid, or a peracid such as 3-chloroperbenzoic acid in a solvent such asdichloromethane or 1,2-dichloroethane, at a temperature of from 0° C. tothe reflux temperature of the solvent.

Intermediates of formula (II) wherein L is chlorine, may be preparedaccording to known procedures, for example by the reaction of thecorresponding carboxylic acid of formula (II) wherein L is replaced byOH, with a suitable halogenating agent, preferably oxalyl chloride orthionyl chloride, in a solvent such as dichloroethane, optionally in thepresence of N,N-dimethylformamide, at a temperature of from 0° C. to thereflux temperature of the solvent.

Intermediates of formula (XII) wherein U is S, and (XIII) wherein V isO, may be prepared according to known procedures, for example by thereaction of a compound of formula (II) as defined above, with an alkalimetal thiocyanate or ammonium thiocyanate or a tetraalkylammoniumthiocyanate for example tetrabutylammonium thiocyanate, generally in thepresence of a base such as an alkali metal carbonate for examplepotassium carbonate, in an inert solvent solvent such as toluene oracetone, at a temperature of from 0° to 100° C.

Intermediate of formula (XII) wherein U is O, may be prepared accordingto known procedures, for example by the reaction of a compound offormula (II) as defined above, with an alkali metal cyanate or ammoniumcyanate or a tetraalkylammonium cyanate for example tetrabutylammoniumcyanate, generally in the presence of a base such as an alkali metalcarbonate for example potassium carbonate, in an inert solvent solventsuch as toluene, at a temperature of from 0° to 100° C.

Collections of compounds of the formula (I) which can be synthesized bythe above mentioned process may also be prepared in a parallel manner,and this may be effected manually or in a semiautomated or fullyautomated manner. In this case, it is possible, for example, to automatethe procedure of the reaction, work-up or purification of the productsor of the intermediates. In total, this is to be understood as meaning aprocedure as is described, for example, by S. H. DeWitt in “AnnualReports in Combinatorial Chemistry and Molecular Diversity: AutomatedSynthesis”, Volume 1, Verlag Escom 1997, pages 69 to 77.

A series of commercially available apparatuses as are offered by, forexample, Stem Corporation, Woodrolfe Road, Tollesbury, Essex, CM9 8SE,England or H+P Labortechnik GmbH, Bruckmannring 28, 85764Oberschleiβheim, Germany or Radleys, Shirehill, Saffron Walden, Essex,England, may be used for the parallel procedure of the reaction andwork-up. For the parallel purification of compounds of the formula (I),or of intermediates obtained during the preparation, use may be made,inter alia, of chromatography apparatuses, for example those by ISCO,Inc., 4700 Superior Street, Lincoln, Nebr. 68504, USA.

The apparatuses mentioned lead to a modular procedure in which theindividual process steps are automated, but manual operations must beperformed between the process steps. This can be prevented by employingsemi-integrated or fully integrated automation systems where theautomation modules in question are operated by, for example, robots.Such automation systems can be obtained, for example, from ZymarkCorporation, Zymark Center, Hopkinton, Mass. 01748, USA.

In addition to what has been described here, compounds of the formula(I) may be prepared in part or fully by solid-phase-supported methods.For this purpose, individual intermediate steps or all intermediatesteps of the synthesis or of a synthesis adapted to suit the procedurein question are bound to a synthetic resin. Solid-phase-supportedsynthesis methods are described extensively in the specialistliterature, for example Barry A. Bunin in “The Combinatorial Index”,Academic Press, 1998.

The use of solid-phase-supported synthesis methods permits a series ofprotocols which are known from the literature and which, in turn, can beperformed manually or in an automated manner. For example, the “tea-bagmethod” (Houghten, U.S. Pat. No. 4,631,211; Houghten et al., Proc. Natl.Acad. Sci, 1985, 82, 5131-5135), in which products by IRORI, 11149 NorthTorrey Pines Road, La Jolla, Calif. 92037, USA, are employed, may besemiautomated. The automation of solid-phase-supported parallelsyntheses is performed successfully, for example, by apparatuses byArgonaut Technologies, Inc., 887 Industrial Road, San Carlos, Calif.94070, USA or MultiSynTech GmbH, Wullener Feld 4, 58454 Witten, Germany.

The preparation of the processes described herein yields compounds ofthe formula (I) in the form of substance collections which are termedlibraries. The present invention also relates to libraries whichcomprise at least two compounds of the formula (I).

Compounds of formula (II), (III), (IV), (V), (VI), (VII), (VIII), (IX),(X), (XI), (XIV) and (XV) are known or may be prepared by known methods.

The following non-limiting Examples illustrate the preparation of thecompounds of formula (I).

CHEMICAL EXAMPLES

NMR spectra were run in deuterochloroform unless stated otherwise. Inthe Examples which follow, quantities (also percentages) areweight-based, unless stated otherwise.

Example 1

Oxalyl chloride (0.15 ml) was added to a suspension of4-trifluoromethyl-3-pyridinecarboxamide (0.25 g) in 1,2-dichloroethaneat 20° C. and then heated to reflux for 2 hours. The mixture was cooled,evaporated and the residue containing4-trifluoromethyl-3-pyridylcarbonyl isocyanate was dissolved intetrahydrofuran. Benzylamine (0.15 ml) was added and the mixture stirredat 20° C. for 2 hours and evaporated. The residue was purified bysilica-gel column chromatography, eluting with n-hexane/ethyl acetate(3:2), to give 1-benzyl-3-(4-trifluoromethyl-3-pyridylcarbonyl)urea(0.30 g, Compound A-37).

By proceeding in a similar manner there was prepared1-benzyl-1-(2-hydroxyethyl)-3-(4-trifluoromethyl-3-pyridylcarbonyl)urea(Compound A-862).

Example 2

Oxalyl chloride (1.50 ml) was added to a suspension of4-trifluoromethyl-3-pyridinecarboxamide (2.0 g) in 1,2-dichloroethane at20° C., and stirred under reflux for 2 hours. The mixture was evaporatedand dichloromethane added to the residue containing4-trifluoromethyl-3-pyridylcarbonyl isocyanate. To this was added at 20°C. a suspension of N,O-dimethylhydroxylamine hydrochloride (2.05 g) andtriethylamine (3.0 ml) in dichloromethane, which had been prepared inadvance. The mixture was stirred for 30 minutes, then water added andthe organic layer dried (magnesium sulfate) and evaporated, to giveafter trituration with ethanol,1-methyl-1-methoxy-3-(4-trifluoromethyl-3-pyridylcarbonyl)urea (2.2 g)(Compound A-313).

By proceeding in a similar manner there was prepared1-hydroxyl-1-isopropyl-3-(4-trifluoromethyl-3-pyridylcarbonyl)urea(Compound A-540).

Example 3

Sodium hydride (0.090 g, 60% dispersion in mineral oil) was added to asolution of 4-trifluoromethyl-3-pyridinecarboxamide (0.40 g) inN,N-dimethylformamide at 20° C., and stirred for 1 hour. Benzylisocyanate (0.31 ml) was added and the mixture stirred at 20° C. for 2hours, then methyl bromoacetate (0.30 ml) added and stirring continuedfor 5 hours. Ethyl acetate and water were added to the solution and theorganic phase dried (magnesium sulfate), evaporated and the residuepurified by column chromatography on silica gel, eluting withn-hexane/ethyl acetate (2:1), to give3-benzyl-1-(4-trifluoromethyl-3-pyridylcarbonyl)hydantoin (0.50 g,Compound S-132).

Example 4

Methanesulfonyl chloride (0.17 ml) was added to an ice-cooled mixture of1-benzyl-1-(2-hydroxyethyl)-3-(4-trifluoromethyl-3-pyridylcarbonyl)urea(0.70 g), and triethylamine (0.64 ml) in dichloromethane, then stirredfor 3 hours at 20° C. The mixture was washed (water), dried (magnesiumsulfate), evaporated and the residue purified by silica-gelchromatography, eluting with n-hexane/ethyl acetate (3:2), to give1-benzyl-3-(4-trifluoromethyl-3-pyridylcarbonyl)-2-imidazolidinone (0.63g, Compound S-15).

Example 5

1,2-Dibromoethane (0.06 ml) was added to a suspension of1-hydroxyl-1-isopropyl-3-(4-trifluoromethyl-3-pyridylcarbonyl)urea (0.20g) and potassium carbonate (0.20 g) in N,N-dimethylformamide at 20° C.,and stirred for 3 hours. Ethyl acetate and water were added and theorganic phase dried (magnesium sulfate), evaporated and the residuepurified by column chromatography on silica gel, eluting withn-hexane/ethyl acetate (2:1), to give2-isopropyl-4-(4-trifluoromethyl-3-pyridylcarbonyl)-perhydro-1,2,4-oxadiazin-3-one(0.25 g, Compound U-3).

Example 6

Oxalyl chloride (3.2 ml, 2M) was added to a suspension of4-trifluoromethylnicotinic acid (1 g) and a catalytic amount ofN,N-dimethylformamide in dichloromethane, and stirred at 20° C. for 1hour. After evaporation, the residue was dissolved in acetone andpotassium thiocyanate (1 g) added with ice bath cooling to give4-trifluoromethyl-3-pyridylcarbonyl isothiocyanate, then N-methylaniline(0.65 g) was added and the mixture stirred at 20° C. for 1 hour. Ethylacetate was added and the mixture washed with water, dried (magnesiumsulfate), evaporated and the residue purified by silica-gelchromatography, eluting with n-hexane/ethyl acetate=2/1, to give1-methyl-1-phenyl-3-(4-trifluoromethyl-3-pyridylcarbonyl)thiourea (0.96g, Compound B-349).

Example 7

Oxalyl chloride (6.4 ml, 2M) was added to a suspension of4-trifluoromethylnicotinic acid (2 g) and a catalytic amount ofN,N-dimethylformamide in dichloromethane, and stirred at 20° C. for 1hour to give a solution of 4-trifluoromethylnicotinic acid chloride.N,N-Ethylenethiourea (2.23 g) was added to sodium hydride (0.82 g, 60%dispersion in mineral oil) in tetrahydrofuran, and the mixture wasstirred at 20° C. for 1 hour, and then added to the above solution of4-trifluoromethylnicotinic acid chloride with ice bath cooling, thenstirred at 20° C. for 1 hour. Ethyl acetate was added and the mixturewashed with water, dried (magnesium sulfate), evaporated and the residuecrystallized (ethanol) to giveN-(4-trifluoromethyl-3-pyridylcarbonyl)-imidazolin-2-thione (1.35 g,Compound S-356).

Example 8

Oxalyl chloride (9.6 ml, 2M) was added to a suspension4-trifluoromethylnicotinic acid (3 g) and a catalytic amount ofN,N-dimethylformamide in dichloromethane, and stirred at 20° C. for 1hour. The mixture was evaporated, the residue dissolved in toluene andtetrabutylammonium thiocyanate (3 g) and potassium carbonate (1.5 g)added, then stirred at 20° C. for 30 minutes to give4-trifluoromethyl-3-pyridylcarbonyl isothiocyanate2,2,2-trifluoroethanol (3.15 g) was then added, and the mixture stirredat 20° C. for 1 hour. Ethyl acetate was added and the mixture washedwith water, hydrochloric acid 1(M), saturated sodium bicarbonate andbrine, dried (magnesium sulfate), evaporated and recrystallised fromethanol to give 2,2,2-trifluoroethylN-(4-trifluoromethyl-3-pyridylcarbonyl)thiocarbamate (1.2 g, CompoundX-45).

Example 9

Allyl bromide (0.10 ml) was added to a suspension of1-methyl-1-methoxy-3-(4-trifluoromethyl-3-pyridylcarbonyl)urea (0.25 g)and potassium carbonate (0.16 g) in N,N-dimethylformamide at 20° C., andstirred for 2 hours. Ethyl acetate and water were added and the organicphase dried (magnesium sulfate), evaporated and the residue purified bycolumn chromatography on silica gel, eluting with n-hexane/ethyl acetate(2:1) to give1-methyl-1-methoxy-3-allyl-3-(4-trifluoromethyl-3-pyridylcarbonyl)urea(0.26 g, Compound E-85).

The following preferred compounds shown in Tables 1 to 9 also form partof the present invention, and were or may be prepared in accordancewith, or analogously to, the above-mentioned Examples 1 to 9 or theabove-described general methods. In the Tables Ph means phenyl. Wheresubscripts are omitted after atoms it will be understood that they areintended, for example CH3 means CH₃.

Compound numbers are given for reference purposes only.

TABLE I Compounds of formula (I) in which R¹ is —C(═U)NR³R⁴; R² is H andm is zero. In Table 1 compounds A-1 to A-881 represent individualcompounds in which U is O, whilst compounds B-1 to B-881 representindividual compounds in which U is S. Compound R³ R⁴ A-1 B-1 CH₃CH═CH HA-2 B-2 CH₂═CHCH₂ H A-3 B-3 CH₃(CH₃)C═CH H A-4 B-4 (CH₃)₂C═CH H A-5 B-5CH₃CH═CHCH₂ H A-6 B-6 CH₂═C(CH₃)CH₂ H A-7 B-7 CH₃CH═C(Cl)CH₂ H A-8 B-8CH₂═CHCH₂CH₂ H A-9 B-9 CH₃CH₂(CH₃)C═CH H A-10 B-10 (CH₃)₂CHCH═CH H A-11B-11 CH₂CH₂CH═CHCH₂ H A-12 B-12 CH₃CH═C(CH₃)CH₂ H A-13 B-13CH(CH₃)HC═CHCH₃ H A-14 B-14 CH₂HC═C(CH₃)₂ H A-15 B-15 CH₃CH═CHCH₂CH₂ HA-16 B-16 CH₂═CH₂CH₂CH₂CH₂ H A-17 B-17 CH₂═CH₂CH₂CH₂CHCH₂ H A-18 B-18CHCCH₂ H A-19 B-19 CH₃CCCH₂ H A-20 B-20 CHCCH(CH₃) H A-21 B-21CH₃CCCH(CH₃) H A-22 B-22 CHCC(CH₃)₂ H A-23 B-23 CH₃CCC(CH₃)₂ H A-24 B-24cyclo-C₃H₅ H A-25 B-25 cyclo-C₃H₄(₁-CH₃) H A-26 B-26 cyclo-C₄H7 H A-27B-27 cyclo-C₄H6(₁-CH₃) H A-28 B-28 cyclo-C₅H9 H A-29 B-29cyclo-C₅H8(₁-CH₃) H A-30 B-30 cyclo-C6H₁₁ H A-31 B-31 cyclo-C6H₁₀(₁-CH₃)H A-32 B-32 (cyclo-C₃H₅)CH₂ H A-33 B-33 (cyclo-C₃H₄(₁-CH₃))CH₂ H A-34B-34 (cyclo-C₄H7)CH₂ H A-35 B-35 (cyclo-C₅H9)CH₂ H A-36 B-36(cyclo-C6H₁₁)CH₂ H A-37 B-37 PhCH₂ H A-38 B-38 PhCH(CH₃) H A-39 B-39PhCH₂CH₂ H A-40 B-40 PhC(CH₃)₂ H A-41 B-41 PhCH₂CH₂ H A-42 B-42(2-F—Ph)CH₂ H A-43 B-43 (3-F—Ph)CH₂ H A-44 B-44 (4-F—Ph)CH₂ H A-45 B-45(2-Cl—Ph)CH₂ H A-46 B-46 (3-Cl—Ph)CH₂ H A-47 B-47 (4-Cl—Ph)CH₂ H A-48B-48 (2-Br—Ph)CH₂ H A-49 B-49 (3-Br—Ph)CH₂ H A-50 B-50 (4-Br—Ph)CH₂ HA-51 B-51 (2-I—Ph)CH₂ H A-52 B-52 (3-I—Ph)CH₂ H A-53 B-53 (4-I—Ph)CH₂ HA-54 B-54 (2-CF₃—Ph)CH₂ H A-55 B-55 (3-CF₃—Ph)CH₂ H A-56 B-56(4-CF₃—Ph)CH₂ H A-57 B-57 (2-CH₃—Ph)CH₂ H A-58 B-58 (3-CH₃—Ph)CH₂ H A-59B-59 (4-CH₃—Ph)CH₂ H A-60 B-60 (2-CH₃O—Ph)CH₂ H A-61 B-61 (3-CH₃O—Ph)CH₂H A-62 B-62 (4-CH₃O—Ph)CH₂ H A-63 B-63 HO H A-64 B-64 CH₃O H A-65 B-65CH₃CH₂O H A-66 B-66 n-C₃H7O H A-67 B-67 iso-C₃H7O H A-68 B-68 n-C₄H9O HA-69 B-69 sec-C₄H9O H A-70 B-70 iso-C₄H9O H A-71 B-71 tert-C₄H9O H A-72B-72 n-C₅H₁₁O H A-73 B-73 n-C6H₁₃O H A-74 B-74 CH₂═CHCH₂O H A-75 B-75CH₂═C(CH₃)CH₂O H A-76 B-76 CH₂═CHCH(CH₃)O H A-77 B-77 CH₂═C(Cl)CH₂O HA-78 B-78 CH₂═CHC(CH₃)₂O H A-79 B-79 CH₃CH═CHCH₂O H A-80 B-80CH₂═CH₂CH₂CH₂O H A-81 B-81 CHCCH₂O H A-82 B-82 CH₃CCCH₂O H A-83 B-83CHCCH(CH₃)O H A-84 B-84 CHCC(CH₃)₂O H A-85 B-85 CH₃CH₂O₂CCH₂O H A-86B-86 PhCH₂O H A-87 B-87 2-CH₃O—PhCH₂O H A-88 B-88 3-CH₃O—PhCH₂O H A-89B-89 4-CH₃O—PhCH₂O H A-90 B-90 PhO H A-91 B-91 2-Cl—PhO H A-92 B-923-Cl—PhO H A-93 B-93 4-Cl—PhO H A-94 B-94 2-CF₃—PhO H A-95 B-953-CF₃—PhO H A-96 B-96 4-CF₃—PhO H A-97 B-97 2-CH₃O—PhO H A-98 B-983-CH₃O—PhO H A-99 B-99 4-CH₃O—PhO H A-100 B-100 NH₂ H A-101 B-101 CH₃NHH A-102 B-102 C₂H₅NH H A-103 B-103 n-C₃H7NH H A-104 B-104 iso-C₃H7NH HA-105 B-105 n-C₄H9NH H A-106 B-106 n-C₅H₁₁NH H A-107 B-107 n-C6H₁₃NH HA-108 B-108 PhCH₂NH H A-109 B-109 PhNH H A-110 B-110 2-F—PhNH H A-111B-111 3-F—PhNH H A-112 B-112 4-F—PhNH H A-113 B-113 2-Cl—PhNH H A-114B-114 3-Cl—PhNH H A-115 B-115 4-Cl—PhNH H A-116 B-116 2-Br—PhNH H A-117B-117 3-Br—PhNH H A-118 B-118 4-Br—PhNH H A-119 B-119 2-I—PhNH H A-120B-120 3-I—PhNH H A-121 B-121 4-I—PhNH H A-122 B-122 2-CF₃—PhNH H A-123B-123 3-CF₃—PhNH H A-124 B-124 4-CF₃—PhNH H A-125 B-125 2-CH₃—PhNH HA-126 B-126 3-CH₃—PhNH H A-127 B-127 4-CH₃—PhNH H A-128 B-1282-CH₃O—PhNH H A-129 B-129 3-CH₃O—PhNH H A-130 B-130 4-CH₃O—PhNH H A-131B-131 2-NO₂—PhNH H A-132 B-132 3-NO₂—PhNH H A-133 B-133 4-NO₂—PhNH HA-134 B-134 2-CN—PhNH H A-135 B-135 3-CN—PhNH H A-136 B-136 4-CN—PhNH HA-137 B-137 Ph(Me)N H A-138 B-138 2-F—Ph(Me)N H A-139 B-139 3-F—Ph(Me)NH A-140 B-140 4-F—Ph(Me)N H A-141 B-141 2-Cl—Ph(Me)N H A-142 B-1423-Cl—Ph(Me)N H A-143 B-143 4-Cl—Ph(Me)N H A-144 B-144 3-CF₃—Ph(Me)N HA-145 B-145 4-CF₃—Ph(Me)N H A-146 B-146 2-CH₃O—Ph(Me)N H A-147 B-1473-CH₃O—Ph(Me)N H A-148 B-148 4-CH₃O—Ph(Me)N H A-149 B-149 Ph H A-150B-150 2-F—Ph H A-151 B-151 3-F—Ph H A-152 B-152 4-F—Ph H A-153 B-1532-Cl—Ph H A-154 B-154 3-Cl—Ph H A-155 B-155 4-Cl—Ph H A-156 B-1562-Br—Ph H A-157 B-157 3-Br—Ph H A-158 B-158 4-Br—Ph H A-159 B-159 2-I—PhH A-160 B-160 3-I—Ph H A-161 B-161 4-I—Ph H A-162 B-162 2-CF₃—Ph H A-163B-163 3-CF₃—Ph H A-164 B-164 4-CF₃—Ph H A-165 B-165 2-CH₃—Ph H A-166B-166 3-CH₃—Ph H A-167 B-167 4-CH₃—Ph H A-168 B-168 2-CH₃O—Ph H A-169B-169 3-CH₃O—Ph H A-170 B-170 4-CH₃O—Ph H A-171 B-171 2-NO₂—Ph H A-172B-172 3-NO₂—Ph H A-173 B-173 4-NO₂—Ph H A-174 B-174 2-CN—Ph H A-175B-175 3-CN—Ph H A-176 B-176 4-CN—Ph H A-177 B-177 2-CO₂H—Ph H A-178B-178 3-CO₂H—Ph H A-179 B-179 4-CO₂H—Ph H A-180 B-180 2-CO₂Me—Ph H A-181B-181 3-CO₂Me—Ph H A-182 B-182 4-CO₂Me—Ph H A-183 B-183 2-HO—Ph H A-184B-184 3-HO—Ph H A-185 B-185 4-HO—Ph H A-186 B-186 2-NH₂—Ph H A-187 B-1873-NH₂—Ph H A-188 B-188 4-NH₂—Ph H A-189 B-189 2-HOCH₂—Ph H A-190 B-1903-HOCH₂—Ph H A-191 B-191 4-HOCH₂—Ph H A-192 B-192 2-CF₃O—Ph H A-193B-193 3-CF₃O—Ph H A-194 B-194 4-CF₃O—Ph H A-195 B-195 2-CF₃CH₂O—Ph HA-196 B-196 3-CF₃CH₂O—Ph H A-197 B-197 4-CF₃CH₂O—Ph H A-198 B-1982-(4-Cl—PhO)—Ph H A-199 B-199 3-(4-Cl—PhO)—Ph H A-200 B-2004-(4-Cl—PhO)—Ph H A-201 B-201 2-(4-CF₃—PhO)—Ph H A-202 B-2023-(4-CF₃—PhO)—Ph H A-203 B-203 4-(4-CF₃—PhO)—Ph H A-204 B-2042,3-diCl—Ph H A-205 B-205 2,5-diCl—Ph H A-206 B-206 2,6-diCl—Ph H A-207B-207 3,4-diCl—Ph H A-208 B-208 3,5-diCl—Ph H A-209 B-209 2-Pyridyl HA-210 B-210 3-Pyridyl H A-211 B-211 4-Pyridyl H A-212 B-212 2-PyrimidylH A-213 B-213 1-Pyrrolyl H A-214 B-214 1-Pyrazolyl H A-215 B-2153-Pyrazolyl H A-216 B-216 1,2,4-Triazol-1-yl H A-217 B-2171,2,4-Triazol-3-yl H A-218 B-218 2-Furanyl H A-219 B-219 3-Furanyl HA-220 B-220 2-Thienyl H A-221 B-221 3-Thienyl H A-222 B-222 2-ThiazolylH A-223 B-223 1,3,4-Thiadiazol-2-yl H A-224 B-224 3-Isoxazolyl H A-225B-225 CH₃CO H A-226 B-226 CH₃CH₂CO H A-227 B-227 n-C₃H7CO H A-228 B-228iso-C₃H7CO H A-229 B-229 n-C₄H9CO H A-230 B-230 iso-C₄H9CO H A-231 B-231sec-C₄H9CO H A-232 B-232 tert-C₄H9CO H A-233 B-233 n-C5H₁₁CO H A-234B-234 n-C6H₁₂CO H A-235 B-235 PhCO H A-236 B-236 PhCH₂CO H A-237 B-237CH₃SO₂ H A-238 B-238 C₂H5SO₂ H A-239 B-239 n-C₃H7SO₂ H A-240 B-240iso-C₃H7SO₂ H A-241 B-241 PhCH₂SO₂ H A-242 B-242 PhSO₂ H A-243 B-2432-Cl—PhSO₂ H A-244 B-244 3-Cl—PhSO₂ H A-245 B-245 4-Cl—PhSO₂ H A-246B-246 CH₃SO₂NH H A-247 B-247 PhSO₂NH H A-248 B-248 CF₃CH₂ H A-249 B-249ClCH₂CH₂ H A-250 B-250 ClCH₂CH₂CH₂ H A-251 B-251 CH₃OCH₂CH₂ H A-252B-252 CH₃CH₂OCH₂CH₂ H A-253 B-253 CH₃OCH₂CH₂CH₂ H A-254 B-254C₂H5OCH₂CH₂CH₂ H A-255 B-255 n-C₄H9OCH₂CH₂CH₂ H A-256 B-256 (CH₃O)₂CHCH₂H A-257 B-257 CH₃CONH H A-258 B-258 PhCONH H A-259 B-259 Ph₂C═N H A-260B-260 HOCH₂CH₂ H A-261 B-261 HOCH₂CH₂CH₂ H A-262 B-262 CH₃O₂CCH₂ H A-263B-263 CH₃O₂CCH(CH₃) H A-264 B-264 CH₃O₂CC(CH₃)₂ H A-265 B-265 NCCH₂ HA-266 B-266 NCCH(CH₃) H A-267 B-267 NCC(CH₃)₂ H A-268 B-268NC(CH₃)(iso-C₃H7)C H A-269 B-269 HOCH₂CH₂CH₂CH₂ H A-270 B-270 CHCCH₂O HA-271 B-271 CH₃O₂CCH₂O H A-272 B-272 CH₃O₂CCH(CH₃)O H A-273 B-273CH₃O₂CC(CH₃)₂O H A-274 B-274 (1-pyrrolidinyl)CH₂CH₂ H A-275 B-275CH₂═CHCH₂ CH₃ A-276 B-276 CH₃CH═CHCH₂ CH₃ A-277 B-277 CH₂═C(CH₃)CH₂ CH₃A-278 B-278 CH₂═CH(CH₃)CH CH₃ A-279 B-279 CH₂═CHCH₂CH₂ CH₃ A-280 B-280CH₃CH═C(CH₃)CH₂ CH₃ A-281 B-281 CH(CH₃)HC═CHCH₃ CH₃ A-282 B-282C(CH₃)₂HC═CH₂ CH₃ A-283 B-283 CH₂HC═C(CH₃)₂ CH₃ A-284 B-284CH₃CH═CHCH₂CH₂ CH₃ A-285 B-285 CH₂═CHCH₂CH₂CH₂ CH₃ A-286 B-286 CHCCH₂CH₃ A-287 B-287 CH₃CCCH₂ CH₃ A-288 B-288 CHCCH(CH₃) CH₃ A-289 B-289CH₃CCCH(CH₃) CH₃ A-290 B-290 cyclo-C₃H5 CH₃ A-291 B-291 cyclo-C5H9 CH₃A-292 B-292 cyclo-C6H₁₁ CH₃ A-293 B-293 (cyclo-C₃H5)CH₂ CH₃ A-294 B-294(cyclo-C5H9)CH₂ CH₃ A-295 B-295 (cyclo-C6H₁₁)CH₂ CH₃ A-296 B-296 PhCH₂CH₃ A-297 B-297 PhCH(CH₃) CH₃ A-298 B-298 PhC(CH₃)₂ CH₃ A-299 B-299PhCH₂CH₂ CH₃ A-300 B-300 (2-F—Ph)CH₂ CH₃ A-301 B-301 (3-F—Ph)CH₂ CH₃A-302 B-302 (4-F—Ph)CH₂ CH₃ A-303 B-303 (2-Cl—Ph)CH₂ CH₃ A-304 B-304(3-Cl—Ph)CH₂ CH₃ A-305 B-305 (4-Cl—Ph)CH₂ CH₃ A-306 B-306 (2-CF₃—Ph)CH₂CH₃ A-307 B-307 (3-CF₃—Ph)CH₂ CH₃ A-308 B-308 (4-CF₃—Ph)CH₂ CH₃ A-309B-309 (2-CH₃O—Ph)CH₂ CH₃ A-310 B-310 (3-CH₃O—Ph)CH₂ CH₃ A-311 B-311(4-CH₃O—Ph)CH₂ CH₃ A-312 B-312 HO CH₃ A-313 B-313 CH₃O CH₃ A-314 B-314CH₃CH₂O CH₃ A-315 B-315 n-C₃H7O CH₃ A-316 B-316 iso-C₃H7O CH₃ A-317B-317 CH₂═CHCH₂O CH₃ A-318 B-318 CH₂═C(CH₃)CH₂O CH₃ A-319 B-319CH₂═CHCH(CH₃)O CH₃ A-320 B-320 CH₂═CHCH(CH₃)O CH₃ A-321 B-321CH₂═CHC(CH₃)₂O CH₃ A-322 B-322 CH₃CH═CHCH₂O CH₃ A-323 B-323 CHCCH₂O CH₃A-324 B-324 CH₃CCCH₂O CH₃ A-325 B-325 CHCCH(CH₃)O CH₃ A-326 B-326CH₃O₂CCH(CH₃)O CH₃ A-327 B-327 CH₃O₂CC(CH₃)₂O CH₃ A-328 B-328 CH₃O₂CCH₂OCH₃ A-329 B-329 PhCH₂O CH₃ A-330 B-330 PhO CH₃ A-331 B-331 NH₂ CH₃ A-332B-332 CH₃NH CH₃ A-333 B-333 C₂H5NH CH₃ A-334 B-334 n-C₃H7NH CH₃ A-335B-335 iso-C₃H7NH CH₃ A-336 B-336 PhCH₂NH CH₃ A-337 B-337 PhNH CH₃ A-338B-338 2-F—PhNH CH₃ A-339 B-339 3-F—PhNH CH₃ A-340 B-340 4-F—PhNH CH₃A-341 B-341 2-Cl—PhNH CH₃ A-342 B-342 3-Cl—PhNH CH₃ A-343 B-3434-Cl—PhNH CH₃ A-344 B-344 2-CF₃—PhNH CH₃ A-345 B-345 3-CF₃—PhNH CH₃A-346 B-346 2-CH₃O—PhNH CH₃ A-347 B-347 3-CH₃O—PhNH CH₃ A-348 B-3484-CH₃O—PhNH CH₃ A-349 B-349 Ph CH₃ A-350 B-350 2-F—Ph CH₃ A-351 B-3513-F—Ph CH₃ A-352 B-352 4-F—Ph CH₃ A-353 B-353 2-Cl—Ph CH₃ A-354 B-3543-Cl—Ph CH₃ A-355 B-355 4-Cl—Ph CH₃ A-356 B-356 2-Br—Ph CH₃ A-357 B-3573-Br—Ph CH₃ A-358 B-358 4-Br—Ph CH₃ A-359 B-359 2-I—Ph CH₃ A-360 B-3603-I—Ph CH₃ A-361 B-361 4-I—Ph CH₃ A-362 B-362 2-CF₃—Ph CH₃ A-363 B-3633-CF₃—Ph CH₃ A-364 B-364 4-CF₃—Ph CH₃ A-365 B-365 2-CH₃—Ph CH₃ A-366B-366 3-CH₃—Ph CH₃ A-367 B-367 4-CH₃—Ph CH₃ A-368 B-368 2-CH₃O—Ph CH₃A-369 B-369 3-CH₃O—Ph CH₃ A-370 B-370 4-CH₃O—Ph CH₃ A-371 B-371 2-NO₂—PhCH₃ A-372 B-372 3-NO₂—Ph CH₃ A-373 B-373 4-NO₂—Ph CH₃ A-374 B-3742-CN—Ph CH₃ A-375 B-375 3-CN—Ph CH₃ A-376 B-376 4-CN—Ph CH₃ A-377 B-3772-CO₂Me—Ph CH₃ A-378 B-378 3-CO₂Me—Ph CH₃ A-379 B-379 4-CO₂Me—Ph CH₃A-380 B-380 2-HO—Ph CH₃ A-381 B-381 3-HO—Ph CH₃ A-382 B-382 4-HO—Ph CH₃A-383 B-383 2-NH₂—Ph CH₃ A-384 B-384 3-NH₂—Ph CH₃ A-385 B-385 4-NH₂—PhCH₃ A-386 B-386 2-CF₃O—Ph CH₃ A-387 B-387 3-CF₃O—Ph CH₃ A-388 B-3884-CF₃O—Ph CH₃ A-389 B-389 4-CF₃CH₂O—Ph CH₃ A-390 B-390 4-(4-Cl—PhO)—PhCH₃ A-391 B-391 4-(4-CF₃—PhO)—Ph CH₃ A-392 B-392 2,3-diCl—Ph CH₃ A-393B-393 2,4-diCl—Ph CH₃ A-394 B-394 2,5-diCl—Ph CH₃ A-395 B-3952,6-diCl—Ph CH₃ A-396 B-396 3,4-diCl—Ph CH₃ A-397 B-397 3,5-diCl—Ph CH₃A-398 B-398 2-Pyridyl CH₃ A-399 B-399 3-Pyridyl CH₃ A-400 B-4004-Pyridyl CH₃ A-401 B-401 2-Pyrimidyl CH₃ A-402 B-402 1-Pyrrolyl CH₃A-403 B-403 1-Pyrazolyl CH₃ A-404 B-404 3-Pyrazolyl CH₃ A-405 B-4051,2,4-Triazol-1-yl CH₃ A-406 B-406 1,2,4-Triazol-3-yl CH₃ A-407 B-4072-Furanyl CH₃ A-408 B-408 3-Furanyl CH₃ A-409 B-409 2-Thienyl CH₃ A-410B-410 3-Thienyl CH₃ A-411 B-411 2-Thiazolyl CH₃ A-412 B-4121,3,4-Thiadiazol-2-yl CH₃ A-413 B-413 3-Isoxazolyl CH₃ A-414 B-414 CH₃COCH₃ A-415 B-415 PhCO CH₃ A-416 B-416 PhCH₂CO CH₃ A-417 B-417 CH₃SO₂NHCH₃ A-418 B-418 PhSO₂NH CH₃ A-419 B-419 CF₃CH₂ CH₃ A-420 B-420 ClCH₂CH₂CH₃ A-421 B-421 ClCH₂CH₂CH₂ CH₃ A-422 B-422 CH₃OCH₂CH₂ CH₃ A-423 B-423CH₃CH₂OCH₂CH₂ CH₃ A-424 B-424 CH₃OCH₂CH₂CH₂ CH₃ A-425 B-425C₂H5OCH₂CH₂CH₂ CH₃ A-426 B-426 n-C₄H9OCH₂CH₂CH₂ CH₃ A-427 B-427(CH₃O)₂CHCH₂ CH₃ A-428 B-428 CH₃CONH CH₃ A-429 B-429 PhCONH CH₃ A-430B-430 Ph₂C═N CH₃ A-431 B-431 HOCH₂CH₂ CH₃ A-432 B-432 HOCH₂CH₂CH₂ CH₃A-433 B-433 CH₃O₂CCH₂ CH₃ A-434 B-434 CH₃O₂CCH(CH₃) CH₃ A-435 B-435CH₃O₂CC(CH₃)₂ CH₃ A-436 B-436 NCCH₂ CH₃ A-437 B-437 NC(CH₃)(iso-C₃H7)CCH₃ A-438 B-438 (1-pyrrolidinyl)CH₂CH₂ C₂H5 A-439 B-439 CH₂═CHCH₂ C₂H5A-440 B-440 CHCCH₂ C₂H5 A-441 B-441 CH₃CCCH₂ C₂H5 A-442 B-442(cyclo-C₃H5)CH₂ C₂H5 A-443 B-443 PhCH₂ C₂H5 A-444 B-444 PhCH₂CH₂ C₂H5A-445 B-445 (2-Cl—Ph)CH₂ C₂H5 A-446 B-446 (3-Cl—Ph)CH₂ C₂H5 A-447 B-447(4-Cl—Ph)CH₂ C₂H5 A-448 B-448 (2-CF₃—Ph)CH₂ C₂H5 A-449 B-449(3-CF₃—Ph)CH₂ C₂H5 A-450 B-450 (4-CF₃—Ph)CH₂ C₂H5 A-451 B-451(2-CH₃O—Ph)CH₂ C₂H5 A-452 B-452 (3-CH₃O—Ph)CH₂ C₂H5 A-453 B-453(4-CH₃O—Ph)CH₂ C₂H5 A-454 B-454 HO C₂H5 A-455 B-455 CH₃O C₂H5 A-456B-456 CH₃CH₂O C₂H5 A-457 B-457 n-C₃H7O C₂H5 A-458 B-458 iso-C₃H7O C₂H5A-459 B-459 CH₂═CHCH₂O C₂H5 A-460 B-460 CHCCH₂O C₂H5 A-461 B-461 PhCH₂OC₂H5 A-462 B-462 PhO C₂H5 A-463 B-463 NH₂ C₂H5 A-464 B-464 CH₃NH C₂H5A-465 B-465 C₂H5NH C₂H5 A-466 B-466 n-C₃H7NH C₂H5 A-467 B-467 iso-C₃H7NHC₂H5 A-468 B-468 PhCH₂NH C₂H5 A-469 B-469 PhNH C₂H5 A-470 B-4702-Cl—PhNH C₂H5 A-471 B-471 3-Cl—PhNH C₂H5 A-472 B-472 4-Cl—PhNH C₂H5A-473 B-473 2-CF₃—PhNH C₂H5 A-474 B-474 3-CF₃—PhNH C₂H5 A-475 B-4752-CH₃O—PhNH C₂H5 A-476 B-476 3-CH₃O—PhNH C₂H5 A-477 B-477 4-CH₃O—PhNHC₂H5 A-478 B-478 Ph C₂H5 A-479 B-479 2-Cl—Ph C₂H5 A-480 B-480 3-Cl—PhC₂H5 A-481 B-481 4-Cl—Ph C₂H5 A-482 B-482 2-CF₃—Ph C₂H5 A-483 B-4833-CF₃—Ph C₂H5 A-484 B-484 4-CF₃—Ph C₂H5 A-485 B-485 2-CH₃O—Ph C₂H5 A-486B-486 3-CH₃O—Ph C₂H5 A-487 B-487 4-CH₃O—Ph C₂H5 A-488 B-488 2-HO—Ph C₂H5A-489 B-489 3-HO—Ph C₂H5 A-490 B-490 4-HO—Ph C₂H5 A-491 B-491 2-NH₂—PhC₂H5 A-492 B-492 3-NH₂—Ph C₂H5 A-493 B-493 4-NH₂—Ph C₂H5 A-494 B-4942-HOCH₂—Ph C₂H5 A-495 B-495 4-CF₃O—Ph C₂H5 A-496 B-496 4-CF₃CH₂O—Ph C₂H5A-497 B-497 4-(4-Cl—PhO)—Ph C₂H5 A-498 B-498 4-(4-CF₃—PhO)—Ph C₂H5 A-499B-499 2,3-diCl—Ph C₂H5 A-500 B-500 1-Pyrrolyl C₂H5 A-501 B-5011-Pyrazolyl C₂H5 A-502 B-502 1,2,4-Triazol-1-yl C₂H5 A-503 B-5032-Thiazolyl C₂H5 A-504 B-504 1,3,4-Thiadiazol-2-yl C₂H5 A-505 B-505CH₃CO C₂H5 A-506 B-506 PhCO C₂H5 A-507 B-507 PhSO₂NH C₂H5 A-508 B-508CF₃CH₂ C₂H5 A-509 B-509 ClCH₂CH₂ C₂H5 A-510 B-510 ClCH₂CH₂CH₂ C₂H5 A-511B-511 CH₃OCH₂CH₂ C₂H5 A-512 B-512 CH₃CH₂OCH₂CH₂ C₂H5 A-513 B-513CH₃OCH₂CH₂CH₂ C₂H5 A-514 B-514 C₂H5OCH₂CH₂CH₂ C₂H5 A-515 B-515n-C₄H9OCH₂CH₂CH₂ C₂H5 A-516 B-516 (CH₃O)₂CHCH₂ C₂H5 A-517 B-517 CH₃CONHC₂H5 A-518 B-518 PhCONH C₂H5 A-519 B-519 HOCH₂CH₂ C₂H5 A-520 B-520HOCH₂CH₂CH₂ C₂H5 A-521 B-521 CH₃O₂CCH₂ C₂H5 A-522 B-522 CH₃O₂CCH(CH₃)C₂H5 A-523 B-523 NCCH₂ n-C₃H7 A-524 B-524 HOCH₂CH₂ n-C₃H7 A-525 B-525CH₂═CHCH₂ iso-C₃H7 A-526 B-526 CHCCH₂ iso-C₃H7 A-527 B-527 CH₃CCCH₂iso-C₃H7 A-528 B-528 (cyclo-C₃H5)CH₂ iso-C₃H7 A-529 B-529 PhCH₂ iso-C₃H7A-530 B-530 PhCH₂CH₂ iso-C₃H7 A-531 B-531 (2-Cl—Ph)CH₂ iso-C₃H7 A-532B-532 (3-Cl—Ph)CH₂ iso-C₃H7 A-533 B-533 (4-Cl—Ph)CH₂ iso-C₃H7 A-534B-534 (2-CF₃—Ph)CH₂ iso-C₃H7 A-535 B-535 (3-CF₃—Ph)CH₂ iso-C₃H7 A-536B-536 (4-CF₃—Ph)CH₂ iso-C₃H7 A-537 B-537 (2-CH₃O—Ph)CH₂ iso-C₃H7 A-538B-538 (3-CH₃O—Ph)CH₂ iso-C₃H7 A-539 B-539 (4-CH₃O—Ph)CH₂ iso-C₃H7 A-540B-540 HO iso-C₃H7 A-541 B-541 CH₃O iso-C₃H7 A-542 B-542 CH₃CH₂O iso-C₃H7A-543 B-543 n-C₃H7O iso-C₃H7 A-544 B-544 iso-C₃H7O iso-C₃H7 A-545 B-545CH₂═CHCH₂O iso-C₃H7 A-546 B-546 CHCCH₂O iso-C₃H7 A-547 B-547 PhCH₂Oiso-C₃H7 A-548 B-548 PhO iso-C₃H7 A-549 B-549 NH₂ iso-C₃H7 A-550 B-550CH₃NH iso-C₃H7 A-551 B-551 C₂H5NH iso-C₃H7 A-552 B-552 n-C₃H7NH iso-C₃H7A-553 B-553 iso-C₃H7NH iso-C₃H7 A-554 B-554 PhCH₂NH iso-C₃H7 A-555 B-555PhNH iso-C₃H7 A-556 B-556 2-Cl—PhNH iso-C₃H7 A-557 B-557 3-Cl—PhNHiso-C₃H7 A-558 B-558 4-Cl—PhNH iso-C₃H7 A-559 B-559 2-CF₃—PhNH iso-C₃H7A-560 B-560 3-CF₃—PhNH iso-C₃H7 A-561 B-561 2-CH₃O—PhNH iso-C₃H7 A-562B-562 3-CH₃O—PhNH iso-C₃H7 A-563 B-563 4-CH₃O—PhNH iso-C₃H7 A-564 B-564Ph iso-C₃H7 A-565 B-565 2-Cl—Ph iso-C₃H7 A-566 B-566 3-Cl—Ph iso-C₃H7A-567 B-567 4-Cl—Ph iso-C₃H7 A-568 B-568 2-CF₃—Ph iso-C₃H7 A-569 B-5693-CF₃—Ph iso-C₃H7 A-570 B-570 4-CF₃—Ph iso-C₃H7 A-571 B-571 2-CH₃O—Phiso-C₃H7 A-572 B-572 3-CH₃O—Ph iso-C₃H7 A-573 B-573 4-CH₃O—Ph iso-C₃H7A-574 B-574 2-HO—Ph iso-C₃H7 A-575 B-575 3-HO—Ph iso-C₃H7 A-576 B-5764-HO—Ph iso-C₃H7 A-577 B-577 2-NH₂—Ph iso-C₃H7 A-578 B-578 3-NH₂—Phiso-C₃H7 A-579 B-579 4-NH₂—Ph iso-C₃H7 A-580 B-580 2-HOCH₂—Ph iso-C₃H7A-581 B-581 4-CF₃O—Ph iso-C₃H7 A-582 B-582 4-CF₃CH₂O—Ph iso-C₃H7 A-583B-583 4-(4-Cl—PhO)—Ph iso-C₃H7 A-584 B-584 4-(4-CF₃—PhO)—Ph iso-C₃H7A-585 B-585 2,3-diCl—Ph iso-C₃H7 A-586 B-586 1-Pyrrolyl iso-C₃H7 A-587B-587 1-Pyrazolyl iso-C₃H7 A-588 B-588 1,2,4-Triazol-1-yl iso-C₃H7 A-589B-589 2-Thiazolyl iso-C₃H7 A-590 B-590 1,3,4-Thiadiazol-₂-yl iso-C₃H7A-591 B-591 CH₃CO iso-C₃H7 A-592 B-592 PhCO iso-C₃H7 A-593 B-593 PhSO₂NHiso-C₃H7 A-594 B-594 CF₃CH₂ iso-C₃H7 A-595 B-595 ClCH₂CH₂ iso-C₃H7 A-596B-596 ClCH₂CH₂CH₂ iso-C₃H7 A-597 B-597 CH₃OCH₂CH₂ iso-C₃H7 A-598 B-598CH₃CH₂OCH₂CH₂ iso-C₃H7 A-599 B-599 CH₃OCH₂CH₂CH₂ iso-C₃H7 A-600 B-600C₂H5OCH₂CH₂CH₂ iso-C₃H7 A-601 B-601 n-C4H9OCH₂CH₂CH₂ iso-C₃H7 A-602B-602 (CH₃O)₂CHCH₂ iso-C₃H7 A-603 B-603 CH₃CONH iso-C₃H7 A-604 B-604PhCONH iso-C₃H7 A-605 B-605 HOCH₂CH₂ iso-C₃H7 A-606 B-606 HOCH₂CH₂CH₂iso-C₃H7 A-607 B-607 CH₃O₂CCH₂ iso-C₃H7 A-608 B-608 CH₃O₂CCH(CH₃)iso-C₃H7 A-609 B-609 NCCH₂ iso-C₃H7 A-610 B-610 NC(CH₃)(iso-C₃H7)tert-C₄H9 A-611 B-611 CH₂═CHCH₂ tert-C₄H9 A-612 B-612 CHCCH₂ tert-C₄H9A-613 B-613 CH₃CCCH₂ tert-C₄H₉ A-614 B-614 (cyclo-C₃H₅)CH₂ tert-C₄H₉A-615 B-615 PhCH₂ tert-C₄H₉ A-616 B-616 PhCH₂CH₂ tert-C₄H₉ A-617 B-617(2-Cl—Ph)CH₂ tert-C₄H₉ A-618 B-618 (3-Cl—Ph)CH₂ tert-C₄H₉ A-619 B-619(4-Cl—Ph)CH₂ tert-C₄H₉ A-620 B-620 (2-CF₃—Ph)CH₂ tert-C₄H₉ A-621 B-621(3-CF₃—Ph)CH₂ tert-C₄H₉ A-622 B-622 (4-CF₃—Ph)CH₂ tert-C₄H₉ A-623 B-623(2-CH₃O—Ph)CH₂ tert-C₄H₉ A-624 B-624 (3-CH₃O—Ph)CH₂ tert-C₄H₉ A-625B-625 (4-CH₃O—Ph)CH₂ tert-C₄H₉ A-626 B-626 HO tert-C₄H₉ A-627 B-627 CH₃Otert-C₄H₉ A-628 B-628 CH₃CH₂O tert-C₄H₉ A-629 B-629 n-C₃H7O tert-C₄H₉A-630 B-630 iso-C₃H7O tert-C₄H₉ A-631 B-631 CH₂═CHCH₂O tert-C₄H₉ A-632B-632 CHCCH₂O tert-C₄H₉ A-633 B-633 PhCH₂O tert-C₄H₉ A-634 B-634 PhOtert-C₄H₉ A-635 B-635 NH₂ tert-C₄H₉ A-636 B-636 CH₃NH tert-C₄H₉ A-637B-637 C₂H5NH tert-C₄H₉ A-638 B-638 n-C₃H7NH tert-C₄H₉ A-639 B-639iso-C₃H7NH tert-C₄H₉ A-640 B-640 PhCH₂NH tert-C₄H₉ A-641 B-641 PhNHtert-C₄H₉ A-642 B-642 2-Cl—PhNH tert-C₄H₉ A-643 B-643 3-Cl—PhNHtert-C₄H₉ A-644 B-644 ₄-Cl—PhNH tert-C₄H₉ A-645 B-645 2-CF₃—PhNHtert-C₄H₉ A-646 B-646 3-CF₃—PhNH tert-C₄H₉ A-647 B-647 2-CH₃O—PhNHtert-C₄H₉ A-648 B-648 3-CH₃O—PhNH tert-C₄H₉ A-649 B-649 4-CH₃O—PhNHtert-C₄H₉ A-650 B-650 Ph tert-C₄H₉ A-651 B-651 2-Cl—Ph tert-C₄H₉ A-652B-652 3-Cl—Ph tert-C₄H₉ A-653 B-653 4-Cl—Ph tert-C₄H₉ A-654 B-6542-CF₃—Ph tert-C₄H₉ A-655 B-655 3-CF₃—Ph tert-C₄H₉ A-656 B-656 4-CF₃—Phtert-C₄H₉ A-657 B-657 2-CH₃O—Ph tert-C₄H₉ A-658 B-658 3-CH₃O—Phtert-C₄H₉ A-659 B-659 4-CH₃O—Ph tert-C₄H₉ A-660 B-660 2-HO—Ph tert-C₄H₉A-661 B-661 3-HO—Ph tert-C₄H₉ A-662 B-662 4-HO—Ph tert-C₄H₉ A-663 B-6632-NH₂—Ph tert-C₄H₉ A-664 B-664 3-NH₂—Ph tert-C₄H₉ A-665 B-665 4-NH₂—Phtert-C₄H₉ A-666 B-666 2-HOCH₂—Ph tert-C₄H₉ A-667 B-667 4-CF₃O—Phtert-C₄H₉ A-668 B-668 4-CF₃CH₂O—Ph tert-C₄H₉ A-669 B-669 4-(4-Cl—PhO)—Phtert-C₄H₉ A-670 B-670 4-(4-CF₃—PhO)—Ph tert-C₄H₉ A-671 B-671 2,3-diCl—Phtert-C₄H₉ A-672 B-672 1-Pyrrolyl tert-C₄H₉ A-673 B-673 1-Pyrazolyltert-C₄H₉ A-674 B-674 1,2,4-Triazol-1-yl tert-C₄H₉ A-675 B-6752-Thiazolyl tert-C₄H₉ A-676 B-676 1,3,4-Thiadiazol-2-yl tert-C₄H₉ A-677B-677 CH₃CO tert-C₄H₉ A-678 B-678 PhCO tert-C₄H₉ A-679 B-679 PhSO₂NHtert-C₄H₉ A-680 B-680 CF₃CH₂ tert-C₄H₉ A-681 B-681 ClCH₂CH₂ tert-C₄H₉A-682 B-682 ClCH₂CH₂CH₂ tert-C₄H₉ A-683 B-683 CH₃OCH₂CH₂ tert-C₄H₉ A-684B-684 CH₃CH₂OCH₂CH₂ tert-C₄H₉ A-685 B-685 CH₃OCH₂CH₂CH₂ tert-C₄H₉ A-686B-686 C₂H5OCH₂CH₂CH₂ tert-C₄H₉ A-687 B-687 n-C₄H9OCH₂CH₂CH₂ tert-C₄H₉A-688 B-688 (CH₃O)₂CHCH₂ tert-C₄H₉ A-689 B-689 CH₃CONH tert-C₄H₉ A-690B-690 PhCONH tert-C₄H₉ A-691 B-691 HOCH₂CH₂ tert-C₄H₉ A-692 B-692HOCH₂CH₂CH₂ tert-C₄H₉ A-693 B-693 CH₃O₂CCH₂ tert-C₄H₉ A-694 B-694CH₃O₂CCH(CH₃) tert-C₄H₉ A-695 B-695 NCCH₂ tert-C₄H₉ A-696 B-696NC(CH₃)(iso-C₃H7)C CH₂═CHCH₂ A-697 B-697 CH₂═CHCH₂ CH₂═CHCH₂ A-698 B-698CHCCH₂ CH₂═CHCH₂ A-699 B-699 CH₃CCCH₂ CH₂═CHCH₂ A-700 B-700(cyclo-C₃H5)CH₂ CH₂═CHCH₂ A-701 B-701 PhCH₂ CH₂═CHCH₂ A-702 B-702PhCH₂CH₂ CH₂═CHCH₂ A-703 B-703 (2-Cl—Ph)CH₂ CH₂═CHCH₂ A-704 B-704(3-Cl—Ph)CH₂ CH₂═CHCH₂ A-705 B-705 (4-Cl—Ph)CH₂ CH₂═CHCH₂ A-706 B-706(2-CF₃—Ph)CH₂ CH₂═CHCH₂ A-707 B-707 (3-CF₃—Ph)CH₂ CH₂═CHCH₂ A-708 B-708(4-CF₃—Ph)CH₂ CH₂═CHCH₂ A-709 B-709 (2-CH₃O—Ph)CH₂ CH₂═CHCH₂ A-710 B-710(3-CH₃O—Ph)CH₂ CH₂═CHCH₂ A-711 B-711 (4-CH₃O—Ph)CH₂ CH₂═CHCH₂ A-712B-712 HO CH₂═CHCH₂ A-713 B-713 CH₃O CH₂═CHCH₂ A-714 B-714 CH₃CH₂OCH₂═CHCH₂ A-715 B-715 n-C₃H7O CH₂═CHCH₂ A-716 B-716 iso-C₃H7O CH₂═CHCH₂A-717 B-717 CH₂═CHCH₂O CH₂═CHCH₂ A-718 B-718 CHCCH₂O CH₂═CHCH₂ A-719B-719 PhCH₂O CH₂═CHCH₂ A-720 B-720 PhO CH₂═CHCH₂ A-721 B-721 NH₂CH₂═CHCH₂ A-722 B-722 CH₃NH CH₂═CHCH₂ A-723 B-723 C₂H5NH CH₂═CHCH₂ A-724B-724 n-C₃H7NH CH₂═CHCH₂ A-725 B-725 iso-C₃H7NH CH₂═CHCH₂ A-726 B-726PhCH₂NH CH₂═CHCH₂ A-727 B-727 PhNH CH₂═CHCH₂ A-728 B-728 2-Cl—PhNHCH₂═CHCH₂ A-729 B-729 3-Cl—PhNH CH₂═CHCH₂ A-730 B-730 4-Cl—PhNHCH₂═CHCH₂ A-731 B-731 2-CF₃—PhNH CH₂═CHCH₂ A-732 B-732 3-CF₃—PhNHCH₂═CHCH₂ A-733 B-733 2-CH₃O—PhNH CH₂═CHCH₂ A-734 B-734 3-CH₃O—PhNHCH₂═CHCH₂ A-735 B-735 4-CH₃O—PhNH CH₂═CHCH₂ A-736 B-736 Ph CH₂═CHCH₂A-737 B-737 2-Cl—Ph CH₂═CHCH₂ A-738 B-738 3-Cl—Ph CH₂═CHCH₂ A-739 B-7394-Cl—Ph CH₂═CHCH₂ A-740 B-740 2-CF₃—Ph CH₂═CHCH₂ A-741 B-741 3-CF₃—PhCH₂═CHCH₂ A-742 B-742 4-CF₃—Ph CH₂═CHCH₂ A-743 B-743 2-CH₃O—Ph CH₂═CHCH₂A-744 B-744 3-CH₃O—Ph CH₂═CHCH₂ A-745 B-745 4-CH₃O—Ph CH₂═CHCH₂ A-746B-746 2-HO—Ph CH₂═CHCH₂ A-747 B-747 3-HO—Ph CH₂═CHCH₂ A-748 B-7484-HO—Ph CH₂═CHCH₂ A-749 B-749 2-NH₂—Ph CH₂═CHCH₂ A-750 B-750 3-NH₂—PhCH₂═CHCH₂ A-751 B-751 4-NH₂—Ph CH₂═CHCH₂ A-752 B-752 2-HOCH₂—PhCH₂═CHCH₂ A-753 B-753 4-CF₃O—Ph CH₂═CHCH₂ A-754 B-754 4-CF₃CH₂O—PhCH₂═CHCH₂ A-755 B-755 4-(4-Cl—PhO)—Ph CH₂═CHCH₂ A-756 B-7564-(4-CF₃—PhO)—Ph CH₂═CHCH₂ A-757 B-757 2,3-diCl—Ph CH₂═CHCH₂ A-758 B-7581-Pyrrolyl CH₂═CHCH₂ A-759 B-759 1-Pyrazolyl CH₂═CHCH₂ A-760 B-7601,2,4-Triazol-1-yl CH₂═CHCH₂ A-761 B-761 2-Thiazolyl CH₂═CHCH₂ A-762B-762 1,3,4-Thiadiazol-2-yl CH₂═CHCH₂ A-763 B-763 CH₃CO CH₂═CHCH₂ A-764B-764 PhCO CH₂═CHCH₂ A-765 B-765 PhSO₂NH CH₂═CHCH₂ A-766 B-766 CF₃CH₂CH₂═CHCH₂ A-767 B-767 ClCH₂CH₂ CH₂═CHCH₂ A-768 B-768 ClCH₂CH₂CH₂CH₂═CHCH₂ A-769 B-769 CH₃OCH₂CH₂ CH₂═CHCH₂ A-770 B-770 CH₃CH₂OCH₂CH₂CH₂═CHCH₂ A-771 B-771 CH₃OCH₂CH₂CH₂ CH₂═CHCH₂ A-772 B-772 C₂H5OCH₂CH₂CH₂CH₂═CHCH₂ A-773 B-773 n-C4H9OCH₂CH₂CH₂ CH₂═CHCH₂ A-774 B-774(CH₃O)₂CHCH₂ CH₂═CHCH₂ A-775 B-775 CH₃CONH CH₂═CHCH₂ A-776 B-776 PhCONHCH₂═CHCH₂ A-777 B-777 HOCH₂CH₂ CH₂═CHCH₂ A-778 B-778 HOCH₂CH₂CH₂CH₂═CHCH₂ A-779 B-779 CH₃O₂CCH₂ CH₂═CHCH₂ A-780 B-780 CH₃O₂CCH(CH₃)CH₂═CHCH₂ A-781 B-781 NCCH₂ CH₂═CHCH₂ A-782 B-782 NC(CH₃)(iso-C₃H7)CPhCH₂ A-783 B-783 CH₂═CHCH₂ PhCH₂ A-784 B-784 CHCCH₂ PhCH₂ A-785 B-785CH₃CCCH₂ PhCH₂ A-786 B-786 (cyclo-C₃H5)CH₂ PhCH₂ A-787 B-787 PhCH₂ PhCH₂A-788 B-788 PhCH₂CH₂ PhCH₂ A-789 B-789 (2-Cl—Ph)CH₂ PhCH₂ A-790 B-790(3-Cl—Ph)CH₂ PhCH₂ A-791 B-791 (4-Cl—Ph)CH₂ PhCH₂ A-792 B-792(2-CF₃—Ph)CH₂ PhCH₂ A-793 B-793 (3-CF₃—Ph)CH₂ PhCH₂ A-794 B-794(4-CF₃—Ph)CH₂ PhCH₂ A-795 B-795 (2-CH₃O—Ph)CH₂ PhCH₂ A-796 B-796(3-CH₃O—Ph)CH₂ PhCH₂ A-797 B-797 (4-CH₃O—Ph)CH₂ PhCH₂ A-798 B-798 HOPhCH₂ A-799 B-799 CH₃O PhCH₂ A-800 B-800 CH₃CH₂O PhCH₂ A-801 B-801n-C₃H7O PhCH₂ A-802 B-802 iso-C₃H7O PhCH₂ A-803 B-803 CH₂═CHCH₂O PhCH₂A-804 B-804 CHCCH₂O PhCH₂ A-805 B-805 PhCH₂O PhCH₂ A-806 B-806 PhO PhCH₂A-807 B-807 NH₂ PhCH₂ A-808 B-808 CH₃NH PhCH₂ A-809 B-809 C₂H5NH PhCH₂A-810 B-810 n-C₃H7NH PhCH₂ A-811 B-811 iso-C₃H7NH PhCH₂ A-812 B-812PhCH₂NH PhCH₂ A-813 B-813 PhNH PhCH₂ A-814 B-814 2-Cl—PhNH PhCH₂ A-815B-815 3-Cl—PhNH PhCH₂ A-816 B-816 4-Cl—PhNH PhCH₂ A-817 B-817 2-CF₃—PhNHPhCH₂ A-818 B-818 3-CF₃—PhNH PhCH₂ A-819 B-819 2-CH₃O—PhNH PhCH₂ A-820B-820 3-CH₃O—PhNH PhCH₂ A-821 B-821 4-CH₃O—PhNH PhCH₂ A-822 B-822 PhPhCH₂ A-823 B-823 2-Cl—Ph PhCH₂ A-824 B-824 3-Cl—Ph PhCH₂ A-825 B-8254-Cl—Ph PhCH₂ A-826 B-826 2-CF₃—Ph PhCH₂ A-827 B-827 3-CF₃—Ph PhCH₂A-828 B-828 4-CF₃—Ph PhCH₂ A-829 B-829 2-CH₃O—Ph PhCH₂ A-830 B-8303-CH₃O—Ph PhCH₂ A-831 B-831 4-CH₃O—Ph PhCH₂ A-832 B-832 2-HO—Ph PhCH₂A-833 B-833 3-HO—Ph PhCH₂ A-834 B-834 4-HO—Ph PhCH₂ A-835 B-835 2-NH₂—PhPhCH₂ A-836 B-836 3-NH₂—Ph PhCH₂ A-837 B-837 4-NH₂—Ph PhCH₂ A-838 B-8382-HOCH₂—Ph PhCH₂ A-839 B-839 4-CF₃O—Ph PhCH₂ A-840 B-840 4-CF₃CH₂O—PhPhCH₂ A-841 B-841 4-(4-Cl—PhO)—Ph PhCH₂ A-842 B-842 4-(4-CF₃—PhO)—PhPhCH₂ A-843 B-843 2,3-diCl—Ph PhCH₂ A-844 B-844 1-Pyrrolyl PhCH₂ A-845B-845 1-Pyrazolyl PhCH₂ A-846 B-846 1,2,4-Triazol-1-yl PhCH₂ A-847 B-8472-Thiazolyl PhCH₂ A-848 B-848 1,3,4-Thiadiazol-2-yl PhCH₂ A-849 B-849CH₃CO PhCH₂ A-850 B-850 PhCO PhCH₂ A-851 B-851 PhSO₂NH PhCH₂ A-852 B-852CF₃CH₂ PhCH₂ A-853 B-853 ClCH₂CH₂ PhCH₂ A-854 B-854 ClCH₂CH₂CH₂ PhCH₂A-855 B-855 CH₃OCH₂CH₂ PhCH₂ A-856 B-856 CH₃CH₂OCH₂CH₂ PhCH₂ A-857 B-857CH₃OCH₂CH₂CH₂ PhCH₂ A-858 B-858 C₂H5OCH₂CH₂CH₂ PhCH₂ A-859 B-859n-C₄H9OCH₂CH₂CH₂ PhCH₂ A-860 B-860 (CH₃O)₂CHCH₂ PhCH₂ A-861 B-861CH(CH₃)CH₂CH₂CH₂CH₂ A-862 B-862 HOCH₂CH₂ PhCH₂ A-863 B-863 CH₂CHBrCH₂CH₂A-864 B-864 CH₂CH(OH)CH₂CH₂ A-865 B-865 CH₂CH═CHCH₂ A-866 B-866benzothiazol-2-yl H A-867 B-867 Ph Ph A-868 B-868 CH₃CONH Ph A-869 B-869HOCH₂CH₂ Ph A-870 B-870 CH₃SO₂OCH₂CH₂CH₂CH₂ H A-871 B-871 CH₂CH₂CH₂CH₂A-872 B-872 CH₂CH₂CH₂CH₂CH₂ A-873 B-873 CH₂CH₂OCH₂CH₂ A-874 B-874CH₂CH₂SCH₂CH₂ A-875 B-875 CH₂CH₂NHCH₂CH₂ A-876 B-876 CH₂CH₂N(CH₃)CH₂CH₂A-877 B-877 N═CHCH₂CH₂ A-878 B-878 Ph NH₂ A-879 B-879 PhCH₂ (CH₃)₂C═NA-880 B-880 Ph (CH₃)₂C═N A-881 B-881 PhCH₂ H

TABLE 2 Compounds of formula (I) in which R¹ is —C(═U)NR³R⁴; U is O, mis zero and R² is as defined hereafter. In Table 2 compounds C-1 toC-151 represent individual compounds in which R² is methyl; compoundsD-1 to D-151 represent individual compounds in which R² is ethyl;compounds E-1 to E-151 represent individual compounds in which R² isallyl; compounds F-1 to F-151 represent individual compounds in which R²is propargyl; compounds G-1 to G-151 represent individual compounds inwhich R² is benzyl; compounds H-1 to H-151 represent individualcompounds in which R² is —CH₂CO₂CH₃; compounds I-1 to I-151 representindividual compounds in which R² is —CH(CH₃)CO₂CH₃; compounds J-1 toJ-151 represent individual compounds in which R² is —CH₂CH(OCH₃)₂.Compound R³ R⁴ C-1 D-1 E-1 F-1 G-1 H-1 I-1 J-1 CH2═CHCH2 H C-2 D-2 E-2F-2 G-2 H-2 I-2 J-2 CH3CH═CHCH2 H C-3 D-3 E-3 F-3 G-3 H-3 I-3 J-3CH2═CHCH2CH2 H C-4 D-4 E-4 F-4 G-4 H-4 I-4 J-4 CHCCH2 H C-5 D-5 E-5 F-5G-5 H-5 I-5 J-5 CH3CCCH2 H C-6 D-6 E-6 F-6 G-6 H-6 I-6 J-6 CHCCH(CH3) HC-7 D-7 E-7 F-7 G-7 H-7 I-7 J-7 cyclo-C3H5 H C-8 D-8 E-8 F-8 G-8 H-8 I-8J-8 cyclo-C5H9 H C-9 D-9 E-9 F-9 G-9 H-9 I-9 J-9 cyclo-C6H11 H C-10 D-10E-10 F-10 G-10 H-10 I-10 J-10 PhCH2 H C-11 D-11 E-11 F-11 G-11 H-11 I-11J-11 PhCH(CH3) H C-12 D-12 E-12 F-12 G-12 H-12 I-12 J-12 NH2 H C-13 D-13E-13 F-13 G-13 H-13 I-13 J-13 CH3NH H C-14 D-14 E-14 F-14 G-14 H-14 I-14J-14 C2H5NH H C-15 D-15 E-15 F-15 G-15 H-15 I-15 J-15 n-C3H7NH H C-16D-16 E-16 F-16 G-16 H-16 I-16 J-16 iso-C3H7NH H C-17 D-17 E-17 F-17 G-17H-17 I-17 J-17 n-C4H9NH H C-18 D-18 E-18 F-18 G-18 H-18 I-18 J-18tert-C4H9NH H C-19 D-19 E-19 F-19 G-19 H-19 I-19 J-19 n-C5H11NH H C-20D-20 E-20 F-20 G-20 H-20 I-20 J-20 n-C6H13NH H C-21 D-21 E-21 F-21 G-21H-21 I-21 J-21 PhCH2NH H C-22 D-22 E-22 F-22 G-22 H-22 I-22 J-22 PhNH HC-23 D-23 E-23 F-23 G-23 H-23 I-23 J-23 HO H C-24 D-24 E-24 F-24 G-24H-24 I-24 J-24 CH3O H C-25 D-25 E-25 F-25 G-25 H-25 I-25 J-25 C2H5O HC-26 D-26 E-26 F-26 G-26 H-26 I-26 J-26 n-C3H7O H C-27 D-27 E-27 F-27G-27 H-27 I-27 J-27 iso-C3H7O H C-28 D-28 E-28 F-28 G-28 H-28 I-28 J-28n-C4H9O H C-29 D-29 E-29 F-29 G-29 H-29 I-29 J-29 tert-C4H9O H C-30 D-30E-30 F-30 G-30 H-30 I-30 J-30 CH2═CHCH2O H C-31 D-31 E-31 F-31 G-31 H-31I-31 J-31 CHCCH2O H C-32 D-32 E-32 F-32 G-32 H-32 I-32 J-32 CH3O2CCH2O HC-33 D-33 E-33 F-33 G-33 H-33 I-33 J-33 CH3O2CCH(CH3)O H C-34 D-34 E-34F-34 G-34 H-34 I-34 J-34 CH3O2CC(CH3)2O H C-35 D-35 E-35 F-35 G-35 H-35I-35 J-35 PhCH2O H C-36 D-36 E-36 F-36 G-36 H-36 I-36 J-36 Ph H C-37D-37 E-37 F-37 G-37 H-37 I-37 J-37 2-F—Ph H C-38 D-38 E-38 F-38 G-38H-38 I-38 J-38 3-F—Ph H C-39 D-39 E-39 F-39 G-39 H-39 I-39 J-39 4-F—Ph HC-40 D-40 E-40 F-40 G-40 H-40 I-40 J-40 2-Cl—Ph H C-41 D-41 E-41 F-41G-41 H-41 I-41 J-41 3-Cl—Ph H C-42 D-42 E-42 F-42 G-42 H-42 I-42 J-424-Cl—Ph H C-43 D-43 E-43 F-43 G-43 H-43 I-43 J-43 2-CF3—Ph H C-44 D-44E-44 F-44 G-44 H-44 I-44 J-44 3-CF3—Ph H C-45 D-45 E-45 F-45 G-45 H-45I-45 J-45 4-CF3—Ph H C-46 D-46 E-46 F-46 G-46 H-46 I-46 J-46 2-CH3—Ph HC-47 D-47 E-47 F-47 G-47 H-47 I-47 J-47 3-CH3—Ph H C-48 D-48 E-48 F-48G-48 H-48 I-48 J-48 4-CH3—Ph H C-49 D-49 E-49 F-49 G-49 H-49 I-49 J-492-CH3O—Ph H C-50 D-50 E-50 F-50 G-50 H-50 I-50 J-50 3-CH3O—Ph H C-51D-51 E-51 F-51 G-51 H-51 I-51 J-51 4-CH3O—Ph H C-52 D-52 E-52 F-52 G-52H-52 I-52 J-52 4-CF3O—Ph H C-53 D-53 E-53 F-53 G-53 H-53 I-53 J-534-CF3CH2O—Ph H C-54 D-54 E-54 F-54 G-54 H-54 I-54 J-54 4-PhO—Ph H C-55D-55 E-55 F-55 G-55 H-55 I-55 J-55 4-(4-Cl—PhO)-Ph H C-56 D-56 E-56 F-56G-56 H-56 I-56 J-56 4-(4-CF3—PhO)-Ph H C-57 D-57 E-57 F-57 G-57 H-57I-57 J-57 CF3CH2 H C-58 D-58 E-58 F-58 G-58 H-58 I-58 J-58 ClCH2CH2 HC-59 D-59 E-59 F-59 G-59 H-59 I-59 J-59 ClCH2CH2CH2 H C-60 D-60 E-60F-60 G-60 H-60 I-60 J-60 CH3OCH2CH2 H C-61 D-61 E-61 F-61 G-61 H-61 I-61J-61 CH3CH2OCH2CH2 H C-62 D-62 E-62 F-62 G-62 H-62 I-62 J-62CH3OCH2CH2CH2 H C-63 D-63 E-63 F-63 G-63 H-63 I-63 J-63 C2H5OCH2CH2CH2 HC-64 D-64 E-64 F-64 G-64 H-64 I-64 J-64 n-C4H9OCH2CH2CH2 H C-65 D-65E-65 F-65 G-65 H-65 I-65 J-65 CH3OCH(CH3)CH2CH2 H C-66 D-66 E-66 F-66G-66 H-66 I-66 J-66 (CH3O)2CHCH2 H C-67 D-67 E-67 F-67 G-67 H-67 I-67J-67 HOCH2CH2 H C-68 D-68 E-68 F-68 G-68 H-68 I-68 J-68 HOCH2CH2CH2 HC-69 D-69 E-69 F-69 G-69 H-69 I-69 J-69 CH3SCH2CH2 H C-70 D-70 E-70 F-70G-70 H-70 I-70 J-70 CH3CH2SCH2CH2 H C-71 D-71 E-71 F-71 G-71 H-71 I-71J-71 CH3SCH2CH2CH2 H C-72 D-72 E-72 F-72 G-72 H-72 I-72 J-72C2H5SCH2CH2CH2 H C-73 D-73 E-73 F-73 G-73 H-73 I-73 J-73 CH2═CHCH2 CH3C-74 D-74 E-74 F-74 G-74 H-74 I-74 J-74 CHCCH2 CH3 C-75 D-75 E-75 F-75G-75 H-75 I-75 J-75 cyclo-C3H5 CH3 C-76 D-76 E-76 F-76 G-76 H-76 I-76J-76 cyclo-C5H9 CH3 C-77 D-77 E-77 F-77 G-77 H-77 I-77 J-77 cyclo-C6H11CH3 C-78 D-78 E-78 F-78 G-78 H-78 I-78 J-78 PhCH2 CH3 C-79 D-79 E-79F-79 G-79 H-79 I-79 J-79 NH2 CH3 C-80 D-80 E-80 F-80 G-80 H-80 I-80 J-80CH3NH CH3 C-81 D-81 E-81 F-81 G-81 H-81 I-81 J-81 C2H5NH CH3 C-82 D-82E-82 F-82 G-82 H-82 I-82 J-82 PhCH2NH CH3 C-83 D-83 E-83 F-83 G-83 H-83I-83 J-83 PhNH CH3 C-84 D-84 E-84 F-84 G-84 H-84 I-84 J-84 HO CH3 C-85D-85 E-85 F-85 G-85 H-85 I-85 J-85 CH3O CH3 C-86 D-86 E-86 F-86 G-86H-86 I-86 J-86 C2H5O CH3 C-87 D-87 E-87 F-87 G-87 H-87 I-87 J-87CH2═CHCH2O CH3 C-88 D-88 E-88 F-88 G-88 H-88 I-88 J-88 CHCCH2O CH3 C-89D-89 E-89 F-89 G-89 H-89 I-89 J-89 CH3O2CCH2O CH3 C-90 D-90 E-90 F-90G-90 H-90 I-90 J-90 CH3O2CCH(CH3)O CH3 C-91 D-91 E-91 F-91 G-91 H-91I-91 J-91 PhCH2O CH3 C-92 D-92 E-92 F-92 G-92 H-92 I-92 J-92 Ph CH3 C-93D-93 E-93 F-93 G-93 H-93 I-93 J-93 4-CF3O—Ph CH3 C-94 D-94 E-94 F-94G-94 H-94 I-94 J-94 4-(4-CF3O)-Ph CH3 C-95 D-95 E-95 F-95 G-95 H-95 I-95J-95 CF3CH2 CH3 C-96 D-96 E-96 F-96 G-96 H-96 I-96 J-96 CH3OCH2CH2 CH3C-97 D-97 E-97 F-97 G-97 H-97 I-97 J-97 CH3CH2OCH2CH2 CH3 C-98 D-98 E-98F-98 G-98 H-98 I-98 J-98 CH3OCH2CH2CH2 CH3 C-99 D-99 E-99 F-99 G-99 H-99I-99 J-99 C2H5OCH2CH2CH2 CH3 C-100 D-100 E-100 F-100 G-100 H-100 I-100J-100 n-C4H9OCH2CH2CH2 CH3 C-101 D-101 E-101 F-101 G-101 H-101 I-101J-101 (CH3O)2CHCH2 CH3 C-102 D-102 E-102 F-102 G-102 H-102 I-102 J-102HOCH2CH2 CH3 C-103 D-103 E-103 F-103 G-103 H-103 I-103 J-103 HOCH2CH2CH2CH3 C-104 D-104 E-104 F-104 G-104 H-104 I-104 J-104 CH3OCH2CH2CH2 CH3C-105 D-105 E-105 F-105 G-105 H-105 I-105 J-105 C2H5OCH2CH2CH2 CH3 C-106D-106 E-106 F-106 G-106 H-106 I-106 J-106 n-C4H9OCH2CH2CH2 CH3 C-107D-107 E-107 F-107 G-107 H-107 I-107 J-107 (CH3O)2CHCH2 CH3 C-108 D-108E-108 F-108 G-108 H-108 I-108 J-108 HOCH2CH2 CH3 C-109 D-109 E-109 F-109G-109 H-109 I-109 J-109 HOCH2CH2CH2 CH3 C-110 D-110 E-110 F-110 G-110H-110 I-110 J-110 CH2═CHCH2 PhCH2 C-111 D-111 E-111 F-111 G-111 H-111I-111 J-111 CHCCH2 PhCH2 C-112 D-112 E-112 F-112 G-112 H-112 I-112 J-112cyclo-C3H5 PhCH2 C-113 D-113 E-113 F-113 G-113 H-113 I-113 J-113cyclo-C5H9 PhCH2 C-114 D-114 E-114 F-114 G-114 H-114 I-114 J-114cyclo-C6H11 PhCH2 C-115 D-115 E-115 F-115 G-115 H-115 I-115 J-115 NH2PhCH2 C-116 D-116 E-116 F-116 G-116 H-116 I-116 J-116 CH3NH PhCH2 C-117D-117 E-117 F-117 G-117 H-117 I-117 J-117 C2H5NH PhCH2 C-118 D-118 E-118F-118 G-118 H-118 I-118 J-118 PhNH PhCH2 C-119 D-119 E-119 F-119 G-119H-119 I-119 J-119 HO PhCH2 C-120 D-120 E-120 F-120 G-120 H-120 I-120J-120 CH3O PhCH2 C-121 D-121 E-121 F-121 G-121 H-121 I-121 J-121 C2H5OPhCH2 C-122 D-122 E-122 F-122 G-122 H-122 I-122 J-122 CH2═CHCH2O PhCH2C-123 D-123 E-123 F-123 G-123 H-123 I-123 J-123 CHCCH2O PhCH2 C-124D-124 E-124 F-124 G-124 H-124 I-124 J-124 CH3O2CCH2O PhCH2 C-125 D-125E-125 F-125 G-125 H-125 I-125 J-125 CH3O2CCH(CH3)O PhCH2 C-126 D-126E-126 F-126 G-126 H-126 I-126 J-126 PhCH2O PhCH2 C-127 D-127 E-127 F-127G-127 H-127 I-127 J-127 Ph PhCH2 C-128 D-128 E-128 F-128 G-128 H-128I-128 J-128 4-CF3O—Ph PhCH2 C-129 D-129 E-129 F-129 G-129 H-129 I-129J-129 4-(4-CF3O)-Ph PhCH2 C-130 D-130 E-130 F-130 G-130 H-130 I-130J-130 CF3CH2 PhCH2 C-131 D-131 E-131 F-131 G-131 H-131 I-131 J-131CH3OCH2CH2 PhCH2 C-132 D-132 E-132 F-132 G-132 H-132 I-132 J-132CH3CH2OCH2CH2 PhCH2 C-133 D-133 E-133 F-133 G-133 H-133 I-133 J-133CH3OCH2CH2CH2 PhCH2 C-134 D-134 E-134 F-134 G-134 H-134 I-134 J-134C2H5OCH2CH2CH2 PhCH2 C-135 D-135 E-135 F-135 G-135 H-135 I-135 J-135n-C4H9OCH2CH2CH2 PhCH2 C-136 D-136 E-136 F-136 G-136 H-136 I-136 J-136(CH3O)2CHCH2 PhCH2 C-137 D-137 E-137 F-137 G-137 H-137 I-137 J-137HOCH2CH2 PhCH2 C-138 D-138 E-138 F-138 G-138 H-138 I-138 J-138HOCH2CH2CH2 PhCH2 C-139 D-139 E-139 F-139 G-139 H-139 I-139 J-139CH3OCH2CH2CH2 PhCH2 C-140 D-140 E-140 F-140 G-140 H-140 I-140 J-140C2H5OCH2CH2CH2 PhCH2 C-141 D-141 E-141 F-141 G-141 H-141 I-141 J-141n-C4H9OCH2CH2CH2 PhCH2 C-142 D-142 E-142 F-142 G-142 H-142 I-142 J-142(CH3O)2CHCH2 PhCH2 C-143 D-143 E-143 F-143 G-143 H-143 I-143 J-143HOCH2CH2 PhCH2 C-144 D-144 E-144 F-144 G-144 H-144 I-144 J-144HOCH2CH2CH2 PhCH2 C-145 D-145 E-145 F-145 G-145 H-145 I-145 J-145CH2CH2CH2CH2 C-146 D-146 E-146 F-146 G-146 H-146 I-146 J-146CH2CH2CH2CH2CH2 C-147 D-147 E-147 F-147 G-147 H-147 I-147 J-147CH2CH2OCH2CH2 C-148 D-148 E-148 F-148 G-148 H-148 I-148 J-148CH2CH2SCH2CH2 C-149 D-149 E-149 F-149 G-149 H-149 I-149 J-149CH2CH2NHCH2CH2 C-150 D-150 E-150 F-150 G-150 H-150 I-150 J-150CH2CH2N(CH3)CH2CH2 C-151 D-151 E-151 F-151 G-151 H-151 I-151 J-151N═CHCH2CH2

TABLE 3 Compounds of formula (I) in which R¹ is —C(═U)NR³R⁴; U is S andm is zero. In Table 3 compounds K-1 to K-151 represent individualcompounds in which R² is methyl; compounds L-1 to L-151 representindividual compounds in which R² is ethyl; compounds M-1 to M-151represent individual compounds in which R² is allyl; compounds N-1 toN-151 represent individual compounds in which R² is propargyl; compoundsO-1 to O-151 represent individual compounds in which R² is benzyl;compounds P-1 to P-151 represent individual compounds in which R² is—CH₂CO₂CH₃; compounds Q-1 to Q-151 represent individual compounds inwhich R² is —CH(CH₃)CO₂CH₃; compounds R-1 to R-151 represent individualcompounds in which R² is —CH₂CH(OCH₃)₂. Compound R³ R⁴ K-1 L-1 M-1 N-1O-1 P-1 Q-1 R-1 CH2═CHCH2 H K-2 L-2 M-2 N-2 O-2 P-2 Q-2 R-2 CH3CH═CHCH2H K-3 L-3 M-3 N-3 O-3 P-3 Q-3 R-3 CH2═CHCH2CH2 H K-4 L-4 M-4 N-4 O-4 P-4Q-4 R-4 CHCCH2 H K-5 L-5 M-5 N-5 O-5 P-5 Q-1 R-5 CH3CCCH2 H K-6 L-6 M-6N-6 O-6 P-6 Q-2 R-6 CHCCH(CH3) H K-7 L-7 M-7 N-7 O-7 P-7 Q-3 R-7cyclo-C3H5 H K-8 L-8 M-8 N-8 O-8 P-8 Q-4 R-8 cyclo-C5H9 H K-9 L-9 M-9N-9 O-9 P-9 Q-1 R-9 cyclo-C6H11 H K-10 L-10 M-10 N-10 O-10 P-10 Q-2 R-10PhCH2 H K-11 L-11 M-11 N-11 O-11 P-11 Q-3 R-11 PhCH(CH3) H K-12 L-12M-12 N-12 O-12 P-12 Q-4 R-12 NH2 H K-13 L-13 M-13 N-13 O-13 P-13 Q-1R-13 CH3NH H K-14 L-14 M-14 N-14 O-14 P-14 Q-2 R-14 C2H5NH H K-15 L-15M-15 N-15 O-15 P-15 Q-3 R-15 n-C3H7NH H K-16 L-16 M-16 N-16 O-16 P-16Q-4 R-16 iso-C3H7NH H K-17 L-17 M-17 N-17 O-17 P-17 Q-1 R-17 n-C4H9NH HK-18 L-18 M-18 N-18 O-18 P-18 Q-2 R-18 tert-C4H9NH H K-19 L-19 M-19 N-19O-19 P-19 Q-3 R-19 n-C5H11NH H K-20 L-20 M-20 N-20 O-20 P-20 Q-4 R-20n-C6H13NH H K-21 L-21 M-21 N-21 O-21 P-21 Q-1 R-21 PhCH2NH H K-22 L-22M-22 N-22 O-22 P-22 Q-2 R-22 PhNH H K-23 L-23 M-23 N-23 O-23 P-23 Q-3R-23 HO H K-24 L-24 M-24 N-24 O-24 P-24 Q-4 R-24 CH3O H K-25 L-25 M-25N-25 O-25 P-25 Q-1 R-25 C2H5O H K-26 L-26 M-26 N-26 O-26 P-26 Q-2 R-26n-C3H7O H K-27 L-27 M-27 N-27 O-27 P-27 Q-3 R-27 iso-C3H7O H K-28 L-28M-28 N-28 O-28 P-28 Q-4 R-28 n-C4H9O H K-29 L-29 M-29 N-29 O-29 P-29 Q-1R-29 tert-C4H9O H K-30 L-30 M-30 N-30 O-30 P-30 Q-2 R-30 CH2═CHCH2O HK-31 L-31 M-31 N-31 O-31 P-31 Q-3 R-31 CHCCH2O H K-32 L-32 M-32 N-32O-32 P-32 Q-4 R-32 CH3O2CCH2O H K-33 L-33 M-33 N-33 O-33 P-33 Q-1 R-33CH3O2CCH(CH3)O H K-34 L-34 M-34 N-34 O-34 P-34 Q-2 R-34 CH3O2CC(CH3)2O HK-35 L-35 M-35 N-35 O-35 P-35 Q-3 R-35 PhCH2O H K-36 L-36 M-36 N-36 O-36P-36 Q-4 R-36 Ph H K-37 L-37 M-37 N-37 O-37 P-37 Q-1 R-37 2-F—Ph H K-38L-38 M-38 N-38 O-38 P-38 Q-2 R-38 3-F—Ph H K-39 L-39 M-39 N-39 O-39 P-39Q-3 R-39 4-F—Ph H K-40 L-40 M-40 N-40 O-40 P-40 Q-4 R-40 2-Cl—Ph H K-41L-41 M-41 N-41 O-41 P-41 Q-1 R-41 3-Cl—Ph H K-42 L-42 M-42 N-42 O-42P-42 Q-2 R-42 4-Cl—Ph H K-43 L-43 M-43 N-43 O-43 P-43 Q-3 R-43 2-CF3—PhH K-44 L-44 M-44 N-44 O-44 P-44 Q-4 R-44 3-CF3—Ph H K-45 L-45 M-45 N-45O-45 P-45 Q-1 R-45 4-CF3—Ph H K-46 L-46 M-46 N-46 O-46 P-46 Q-2 R-462-CH3—Ph H K-47 L-47 M-47 N-47 O-47 P-47 Q-3 R-47 3-CH3—Ph H K-48 L-48M-48 N-48 O-48 P-48 Q-4 R-48 4-CH3—Ph H K-49 L-49 M-49 N-49 O-49 P-49Q-1 R-49 2-CH3O—Ph H K-50 L-50 M-50 N-50 O-50 P-50 Q-2 R-50 3-CH3O—Ph HK-51 L-51 M-51 N-51 O-51 P-51 Q-3 R-51 4-CH3O—Ph H K-52 L-52 M-52 N-52O-52 P-52 Q-4 R-52 4-CF3O—Ph H K-53 L-53 M-53 N-53 O-53 P-53 Q-1 R-534-CF3CH2O—Ph H K-54 L-54 M-54 N-54 O-54 P-54 Q-2 R-54 4-PhO—Ph H K-55L-55 M-55 N-55 O-55 P-55 Q-3 R-55 4-(4-Cl—PhO)-Ph H K-56 L-56 M-56 N-56O-56 P-56 Q-4 R-56 4-(4-CF3—PhO)-Ph H K-57 L-57 M-57 N-57 O-57 P-57 Q-1R-57 CF3CH2 H K-58 L-58 M-58 N-58 O-58 P-58 Q-2 R-58 ClCH2CH2 H K-59L-59 M-59 N-59 O-59 P-59 Q-3 R-59 ClCH2CH2CH2 H K-60 L-60 M-60 N-60 O-60P-60 Q-4 R-60 CH3OCH2CH2 H K-61 L-61 M-61 N-61 O-61 P-61 Q-1 R-61CH3CH2OCH2CH2 H K-62 L-62 M-62 N-62 O-62 P-62 Q-2 R-62 CH3OCH2CH2CH2 HK-63 L-63 M-63 N-63 O-63 P-63 Q-3 R-63 C2H5OCH2CH2CH2 H K-64 L-64 M-64N-64 O-64 P-64 Q-4 R-64 n-C4H9OCH2CH2CH2 H K-65 L-65 M-65 N-65 O-65 P-65Q-1 R-65 CH3OCH(CH3)CH2CH2 H K-66 L-66 M-66 N-66 O-66 P-66 Q-2 R-66(CH3O)2CHCH2 H K-67 L-67 M-67 N-67 O-67 P-67 Q-3 R-67 HOCH2CH2 H K-68L-68 M-68 N-68 O-68 P-68 Q-4 R-68 HOCH2CH2CH2 H K-69 L-69 M-69 N-69 O-69P-69 Q-1 R-69 CH3SCH2CH2 H K-70 L-70 M-70 N-70 O-70 P-70 Q-2 R-70CH3CH2SCH2CH2 H K-71 L-71 M-71 N-71 O-71 P-71 Q-3 R-71 CH3SCH2CH2CH2 HK-72 L-72 M-72 N-72 O-72 P-72 Q-4 R-72 C2H5SCH2CH2CH2 H K-73 L-73 M-73N-73 O-73 P-73 Q-1 R-73 CH2═CHCH2 CH3 K-74 L-74 M-74 N-74 O-74 P-74 Q-2R-74 CHCCH2 CH3 K-75 L-75 M-75 N-75 O-75 P-75 Q-3 R-75 cyclo-C3H5 CH3K-76 L-76 M-76 N-76 O-76 P-76 Q-4 R-76 cyclo-C5H9 CH3 K-77 L-77 M-77N-77 O-77 P-77 Q-1 R-77 cyclo-C6H11 CH3 K-78 L-78 M-78 N-78 O-78 P-78Q-2 R-78 PhCH2 CH3 K-79 L-79 M-79 N-79 O-79 P-79 Q-3 R-79 NH2 CH3 K-80L-80 M-80 N-80 O-80 P-80 Q-4 R-80 CH3NH CH3 K-81 L-81 M-81 N-81 O-81P-81 Q-1 R-81 C2H5NH CH3 K-82 L-82 M-82 N-82 O-82 P-82 Q-2 R-82 PhCH2NHCH3 K-83 L-83 M-83 N-83 O-83 P-83 Q-3 R-83 PhNH CH3 K-84 L-84 M-84 N-84O-84 P-84 Q-4 R-84 HO CH3 K-85 L-85 M-85 N-85 O-85 P-85 Q-1 R-85 CH3OCH3 K-86 L-86 M-86 N-86 O-86 P-86 Q-2 R-86 C2H5O CH3 K-87 L-87 M-87 N-87O-87 P-87 Q-3 R-87 CH2═CHCH2O CH3 K-88 L-88 M-88 N-88 O-88 P-88 Q-4 R-88CHCCH2O CH3 K-89 L-89 M-89 N-89 O-89 P-89 Q-1 R-89 CH3O2CCH2O CH3 K-90L-90 M-90 N-90 O-90 P-90 Q-2 R-90 CH3O2CCH(CH3)O CH3 K-91 L-91 M-91 N-91O-91 P-91 Q-3 R-91 PhCH2O CH3 K-92 L-92 M-92 N-92 O-92 P-92 Q-4 R-92 PhCH3 K-93 L-93 M-93 N-93 O-93 P-93 Q-1 R-93 4-CF3O—Ph CH3 K-94 L-94 M-94N-94 O-94 P-94 Q-2 R-94 4-(4-CF3O)-Ph CH3 K-95 L-95 M-95 N-95 O-95 P-95Q-3 R-95 CF3CH2 CH3 K-96 L-96 M-96 N-96 O-96 P-96 Q-4 R-96 CH3OCH2CH2CH3 K-97 L-97 M-97 N-97 O-97 P-97 Q-1 R-97 CH3CH2OCH2CH2 CH3 K-98 L-98M-98 N-98 O-98 P-98 Q-2 R-98 CH3OCH2CH2CH2 CH3 K-99 L-99 M-99 N-99 O-99P-99 Q-3 R-99 C2H5OCH2CH2CH2 CH3 K-100 L-100 M-100 N-100 O-100 P-100 Q-4R-100 n-C4H9OCH2CH2CH2 CH3 K-101 L-101 M-101 N-101 O-101 P-101 Q-1 R-101(CH3O)2CHCH2 CH3 K-102 L-102 M-102 N-102 O-102 P-102 Q-2 R-102 HOCH2CH2CH3 K-103 L-103 M-103 N-103 O-103 P-103 Q-3 R-103 HOCH2CH2CH2 CH3 K-104L-104 M-104 N-104 O-104 P-104 Q-4 R-104 CH3OCH2CH2CH2 CH3 K-105 L-105M-105 N-105 O-105 P-105 Q-1 R-105 C2H5OCH2CH2CH2 CH3 K-106 L-106 M-106N-106 O-106 P-106 Q-2 R-106 n-C4H9OCH2CH2CH2 CH3 K-107 L-107 M-107 N-107O-107 P-107 Q-3 R-107 (CH3O)2CHCH2 CH3 K-108 L-108 M-108 N-108 O-108P-108 Q-4 R-108 HOCH2CH2 CH3 K-109 L-109 M-109 N-109 O-109 P-109 Q-1R-109 HOCH2CH2CH2 CH3 K-110 L-110 M-110 N-110 O-110 P-110 Q-2 R-110CH2═CHCH2 PhCH2 K-111 L-111 M-111 N-111 O-111 P-111 Q-3 R-111 CHCCH2PhCH2 K-112 L-112 M-112 N-112 O-112 P-112 Q-4 R-112 cyclo-C3H5 PhCH2K-113 L-113 M-113 N-113 O-113 P-113 Q-1 R-113 cyclo-C5H9 PhCH2 K-114L-114 M-114 N-114 O-114 P-114 Q-2 R-114 cyclo-C6H11 PhCH2 K-115 L-115M-115 N-115 O-115 P-115 Q-3 R-115 NH2 PhCH2 K-116 L-116 M-116 N-116O-116 P-116 Q-4 R-116 CH3NH PhCH2 K-117 L-117 M-117 N-117 O-117 P-117Q-1 R-117 C2H5NH PhCH2 K-118 L-118 M-118 N-118 O-118 P-118 Q-2 R-118PhNH PhCH2 K-119 L-119 M-119 N-119 O-119 P-119 Q-3 R-119 HO PhCH2 K-120L-120 M-120 N-120 O-120 P-120 Q-4 R-120 CH3O PhCH2 K-121 L-121 M-121N-121 O-121 P-121 Q-1 R-121 C2H5O PhCH2 K-122 L-122 M-122 N-122 O-122P-122 Q-2 R-122 CH2═CHCH2O PhCH2 K-123 L-123 M-123 N-123 O-123 P-123 Q-3R-123 CHCCH2O PhCH2 K-124 L-124 M-124 N-124 O-124 P-124 Q-4 R-124CH3O2CCH2O PhCH2 K-125 L-125 M-125 N-125 O-125 P-125 Q-1 R-125CH3O2CCH(CH3)O PhCH2 K-126 L-126 M-126 N-126 O-126 P-126 Q-2 R-126PhCH2O PhCH2 K-127 L-127 M-127 N-127 O-127 P-127 Q-3 R-127 Ph PhCH2K-128 L-128 M-128 N-128 O-128 P-128 Q-4 R-128 4-CF3O—Ph PhCH2 K-129L-129 M-129 N-129 O-129 P-129 Q-1 R-129 4-(4-CF3O)-Ph PhCH2 K-130 L-130M-130 N-130 O-130 P-130 Q-2 R-130 CF3CH2 PhCH2 K-131 L-131 M-131 N-131O-131 P-131 Q-3 R-131 CH3OCH2CH2 PhCH2 K-132 L-132 M-132 N-132 O-132P-132 Q-4 R-132 CH3CH2OCH2CH2 PhCH2 K-133 L-133 M-133 N-133 O-133 P-133Q-1 R-133 CH3OCH2CH2CH2 PhCH2 K-134 L-134 M-134 N-134 O-134 P-134 Q-2R-134 C2H5OCH2CH2CH2 PhCH2 K-135 L-135 M-135 N-135 O-135 P-135 Q-3 R-135n-C4H9OCH2CH2CH2 PhCH2 K-136 L-136 M-136 N-136 O-136 P-136 Q-4 R-136(CH3O)2CHCH2 PhCH2 K-137 L-137 M-137 N-137 O-137 P-137 Q-1 R-137HOCH2CH2 PhCH2 K-138 L-138 M-138 N-138 O-138 P-138 Q-2 R-138 HOCH2CH2CH2PhCH2 K-139 L-139 M-139 N-139 O-139 P-139 Q-3 R-139 CH3OCH2CH2CH2 PhCH2K-140 L-140 M-140 N-140 O-140 P-140 Q-4 R-140 C2H5OCH2CH2CH2 PhCH2 K-141L-141 M-141 N-141 O-141 P-141 Q-1 R-141 n-C4H9OCH2CH2CH2 PhCH2 K-142L-142 M-142 N-142 O-142 P-142 Q-2 R-142 (CH3O)2CHCH2 PhCH2 K-143 L-143M-143 N-143 O-143 P-143 Q-3 R-143 HOCH2CH2 PhCH2 K-144 L-144 M-144 N-144O-144 P-144 Q-4 R-144 HOCH2CH2CH2 PhCH2 K-145 L-145 M-145 N-145 O-145P-145 Q-1 R-145 CH2CH2CH2CH2 K-146 L-146 M-146 N-146 O-146 P-146 Q-2R-146 CH2CH2CH2CH2CH2 K-147 L-147 M-147 N-147 O-147 P-147 Q-3 R-147CH2CH2OCH2CH2 K-148 L-148 M-148 N-148 O-148 P-148 Q-4 R-148CH2CH2SCH2CH2 K-149 L-149 M-149 N-149 O-149 P-149 Q-1 R-149CH2CH2NHCH2CH2 K-150 L-150 M-150 N-150 O-150 P-150 Q-2 R-150CH2CH2N(CH3)CH2CH2 K-151 L-151 M-151 N-151 O-151 P-151 Q-3 R-151N═CHCH2CH2

TABLE 4 Compounds of formula (IA): (IA)

Com- pound U R⁷ R⁸ W R⁴ S-1 O H H CH2 H S-2 O H H CH2 n-C3H7 S-3 O H HCH2 iso-C3H7 S-4 O H H CH2 n-C4H9 S-5 O H H CH2 iso-C4H9 S-6 O H H CH2sec-C4H9 S-7 O H H CH2 tert-C4H9 S-8 O H H CH2 n-C5H11 S-9 O H H CH2n-C6H13 S-10 O H H CH2 cyclo-C3H5 S-11 O H H CH2 cyclo-C5H9 S-12 O H HCH2 cyclo-C6H11 S-13 O H H CH2 CH2═CHCH2 S-14 O H H CH2 CHCCH2 S-15 O HH CH2 PhCH2 S-16 O H H CH2 Ph(CH3)CH S-17 O H H CH2 Ph(CH3)2C S-18 O H HCH2 Ph S-19 O H H CH2 2-Cl—Ph S-20 O H H CH2 3-Cl—Ph S-21 O H H CH24-Cl—Ph S-22 O H H CH2 4-CF3O—Ph S-23 O H H CH2 4-(4-CF3—PhO)—Ph S-24 OCH3 H CH2 C2H5 S-25 O CH3 H CH2 n-C3H7 S-26 O CH3 H CH2 iso-C3H7 S-27 OCH3 H CH2 n-C4H9 S-28 O CH3 H CH2 iso-C4H9 S-29 O CH3 H CH2 sec-C4H9S-30 O CH3 H CH2 tert-C4H9 S-31 O CH3 H CH2 n-C5H11 S-32 O CH3 H CH2n-C6H13 S-33 O CH3 H CH2 cyclo-C3H5 S-34 O CH3 H CH2 cyclo-C5H9 S-35 OCH3 H CH2 cyclo-C6H11 S-36 O CH3 H CH2 CH2═CHCH2 S-37 O CH3 H CH2 CHCCH2S-38 O CH3 H CH2 PhCH2 S-39 O CH3 H CH2 Ph(CH3)CH S-40 O CH3 H CH2Ph(CH3)2C S-41 O CH3 H CH2 Ph S-42 O CH3 H CH2 2-Cl—Ph S-43 O CH3 H CH23-Cl—Ph S-44 O CH3 H CH2 4-Cl—Ph S-45 O CH3 H CH2 4-CF3O—Ph S-46 O CH3 HCH2 4-(4-CF3—PhO)—Ph S-47 O CH3 CH3 CH2 CH3 S-48 O CH3 CH3 CH2 C2H5 S-49O CH3 CH3 CH2 n-C3H7 S-50 O CH3 CH3 CH2 iso-C3H7 S-51 O CH3 CH3 CH2n-C4H9 S-52 O CH3 CH3 CH2 iso-C4H9 S-53 O CH3 CH3 CH2 sec-C4H9 S-54 OCH3 CH3 CH2 tert-C4H9 S-55 O CH3 CH3 CH2 n-C5H11 S-56 O CH3 CH3 CH2n-C6H13 S-57 O CH3 CH3 CH2 cyclo-C3H5 S-58 O CH3 CH3 CH2 cyclo-C5H9 S-59O CH3 CH3 CH2 cyclo-C6H11 S-60 O CH3 CH3 CH2 CH2═CHCH2 S-61 O CH3 CH3CH2 CHCCH2 S-62 O CH3 CH3 CH2 PhCH2 S-63 O CH3 CH3 CH2 Ph(CH3)CH S-64 OCH3 CH3 CH2 Ph(CH3)2C S-65 O CH3 CH3 CH2 Ph S-66 O CH3 CH3 CH2 2-Cl—PhS-67 O CH3 CH3 CH2 3-Cl—Ph S-68 O CH3 CH3 CH2 4-Cl—Ph S-69 O CH3 CH3 CH24-CF3O—Ph S-70 O CH3 CH3 CH2 4-(4-CF3—PhO)—Ph S-71 O OCH3 H CH2 C2H5S-72 O OCH3 H CH2 n-C3H7 S-73 O OCH3 H CH2 iso-C3H7 S-74 O OCH3 H CH2n-C4H9 S-75 O OCH3 H CH2 iso-C4H9 S-76 O OCH3 H CH2 sec-C4H9 S-77 O OCH3H CH2 tert-C4H9 S-78 O OCH3 H CH2 n-C5H11 S-79 O OCH3 H CH2 n-C6H13 S-80O OCH3 H CH2 cyclo-C3H5 S-81 O OCH3 H CH2 cyclo-C5H9 S-82 O OCH3 H CH2cyclo-C6H11 S-83 O OCH3 H CH2 CH2═CHCH2 S-84 O OCH3 H CH2 CHCCH2 S-85 OOCH3 H CH2 PhCH2 S-86 O OCH3 H CH2 Ph(CH3)CH S-87 O OCH3 H CH2 Ph(CH3)2CS-88 O OCH3 H CH2 Ph S-89 O OCH3 H CH2 2-Cl—Ph S-90 O OCH3 H CH2 3-Cl—PhS-91 O OCH3 H CH2 4-Cl—Ph S-92 O OCH3 H CH2 4-CF3O—Ph S-93 O OCH3 H CH24-(4-CF3—PhO)—Ph S-94 O OCH2CH3 H CH2 CH3 S-95 O OCH2CH3 H CH2 C2H5 S-96O OCH2CH3 H CH2 n-C3H7 S-97 O OCH2CH3 H CH2 iso-C3H7 S-98 O OCH2CH3 HCH2 n-C4H9 S-99 O OCH2CH3 H CH2 iso-C4H9 S-100 O OCH2CH3 H CH2 sec-C4H9S-101 O OCH2CH3 H CH2 tert-C4H9 S-102 O OCH2CH3 H CH2 n-C5H11 S-103 OOCH2CH3 H CH2 n-C6H13 S-104 O OCH2CH3 H CH2 cyclo-C3H5 S-105 O OCH2CH3 HCH2 cyclo-C5H9 S-106 O OCH2CH3 H CH2 cyclo-C6H11 S-107 O OCH2CH3 H CH2CH2═CHCH2 S-108 O OCH2CH3 H CH2 CHCCH2 S-109 O OCH2CH3 H CH2 PhCH2 S-110O OCH2CH3 H CH2 Ph(CH3)CH S-111 O OCH2CH3 H CH2 Ph(CH3)2C S-112 OOCH2CH3 H CH2 Ph S-113 O OCH2CH3 H CH2 2-Cl—Ph S-114 O OCH2CH3 H CH23-Cl—Ph S-115 O OCH2CH3 H CH2 4-Cl—Ph S-116 O OCH2CH3 H CH2 4-CF3O—PhS-117 O OCH2CH3 H CH2 4-(4-CF3—PhO)—Ph S-118 O H H C═O H S-119 O H H C═On-C3H7 S-120 O H H C═O iso-C3H7 S-121 O H H C═O n-C4H9 S-122 O H H C═Oiso-C4H9 S-123 O H H C═O sec-C4H9 S-124 O H H C═O tert-C4H9 S-125 O H HC═O n-C5H11 S-126 O H H C═O n-C6H13 S-127 O H H C═O cyclo-C3H5 S-128 O HH C═O cycto-C5H9 S-129 O H H C═O cyclo-C6H11 S-130 O H H C═O CH2═CHCH2S-131 O H H C═O CHCCH2 S-132 O H H C═O PhCH2 S-133 O H H C═O Ph(CH3)CHS-134 O H H C═O Ph(CH3)2C S-135 O H H C═O Ph S-136 O H H C═O 2-Cl—PhS-137 O H H C═O 3-Cl—Ph S-138 O H H C═O 4-Cl—Ph S-139 O H H C═O4-CF3O—Ph S-140 O H H C═O 4-(4-CF3—PhO)—Ph S-141 O CH3 H C═O C2H5 S-142O CH3 H C═O n-C3H7 S-143 O CH3 H C═O iso-C3H7 S-144 O CH3 H C═O n-C4H9S-145 O CH3 H C═O iso-C4H9 S-146 O CH3 H C═O sec-C4H9 S-147 O CH3 H C═Otert-C4H9 S-148 O CH3 H C═O n-C5H11 S-149 O CH3 H C═O n-C6H13 S-150 OCH3 H C═O cyclo-C3H5 S-151 O CH3 H C═O cyclo-C5H9 S-152 O CH3 H C═Ocyclo-C6H11 S-153 O CH3 H C═O CH2═CHCH2 S-154 O CH3 H C═O CHCCH2 S-155 OCH3 H C═O PhCH2 S-156 O CH3 H C═O Ph(CH3)CH S-157 O CH3 H C═O Ph(CH3)2CS-158 O CH3 H C═O Ph S-159 O CH3 H C═O 2-Cl—Ph S-160 O CH3 H C═O 3-Cl—PhS-161 O CH3 H C═O 4-Cl—Ph S-162 O CH3 H C═O 4-CF3O—Ph S-163 O CH3 H C═O4-(4-CF3—PhO)—Ph S-164 O CH3 CH3 C═O CH3 S-165 O CH3 CH3 C═O C2H5 S-166O CH3 CH3 C═O n-C3H7 S-167 O CH3 CH3 C═O iso-C3H7 S-168 O CH3 CH3 C═On-C4H9 S-169 O CH3 CH3 C═O iso-C4H9 S-170 O CH3 CH3 C═O sec-C4H9 S-171 OCH3 CH3 C═O tert-C4H9 S-172 O CH3 CH3 C═O n-C5H11 S-173 O CH3 CH3 C═On-C6H13 S-174 O CH3 CH3 C═O cyclo-C3H5 S-175 O CH3 CH3 C═O cyclo-C5H9S-176 O CH3 CH3 C═O cyclo-C6H11 S-177 O CH3 CH3 C═O CH2═CHCH2 S-178 OCH3 CH3 C═O CHCCH2 S-179 O CH3 CH3 C═O PhCH2 S-180 O CH3 CH3 C═OPh(CH3)CH S-181 O CH3 CH3 C═O Ph(CH3)2C S-182 O CH3 CH3 C═O Ph S-183 OCH3 CH3 C═O 2-Cl—Ph S-184 O CH3 CH3 C═O 3-Cl—Ph S-185 O CH3 CH3 C═O4-Cl—Ph S-186 O CH3 CH3 C═O 4-CF3O—Ph S-187 O CH3 CH3 C═O4-(4-CF3—PhO)—Ph S-188 O OCH3 H C═O C2H5 S-189 O OCH3 H C═O n-C3H7 S-190O OCH3 H C═O iso-C3H7 S-191 O OCH3 H C═O n-C4H9 S-192 O OCH3 H C═Oiso-C4H9 S-193 O OCH3 H C═O sec-C4H9 S-194 O OCH3 H C═O tert-C4H9 S-195O OCH3 H C═O n-C5H11 S-196 O OCH3 H C═O n-C6H13 S-197 O OCH3 H C═Ocyclo-C3H5 S-198 O OCH3 H C═O cyclo-C5H9 S-199 O OCH3 H C═O cyclo-C6H11S-200 O OCH3 H C═O CH2═CHCH2 S-201 O OCH3 H C═O CHCCH2 S-202 O OCH3 HC═O PhCH2 S-203 O OCH3 H C═O Ph(CH3)CH S-204 O OCH3 H C═O Ph(CH3)2CS-205 O OCH3 H C═O Ph S-206 O OCH3 H C═O 2-Cl—Ph S-207 O OCH3 H C═O3-Cl—Ph S-208 O OCH3 H C═O 4-Cl—Ph S-209 O OCH3 H C═O 4-CF3O—Ph S-210 OOCH3 H C═O 4-(4-CF3—PhO)—Ph S-211 O OCH2CH3 H C═O CH3 S-212 O OCH2CH3 HC═O C2H5 S-213 O OCH2CH3 H C═O n-C3H7 S-214 O OCH2CH3 H C═O iso-C3H7S-215 O OCH2CH3 H C═O n-C4H9 S-216 O OCH2CH3 H C═O iso-C4H9 S-217 OOCH2CH3 H C═O sec-C4H9 S-218 O OCH2CH3 H C═O tert-C4H9 S-219 O OCH2CH3 HC═O n-C5H11 S-220 O OCH2CH3 H C═O n-C6H13 S-221 O OCH2CH3 H C═Ocyclo-C3H5 S-222 O OCH2CH3 H C═O cyclo-C5H9 S-223 O OCH2CH3 H C═Ocyclo-C6H11 S-224 O OCH2CH3 H C═O CH2═CHCH2 S-225 O OCH2CH3 H C═O CHCCH2S-226 O OCH2CH3 H C═O PhCH2 S-227 O OCH2CH3 H C═O Ph(CH3)CH S-228 OOCH2CH3 H C═O Ph(CH3)2C S-229 O OCH2CH3 H C═O Ph S-230 O OCH2CH3 H C═O2-Cl—Ph S-231 O OCH2CH3 H C═O 3-Cl—Ph S-232 O OCH2CH3 H C═O 4-Cl—PhS-233 O OCH2CH3 H C═O 4-CF3O—Ph S-234 O OCH2CH3 H C═O 4-(4-CF3—PhO)—PhS-235 O H H CH2CH2 C2H5 S-236 O H H CH2CH2 n-C3H7 S-237 O H H CH2CH2iso-C3H7 S-238 O H H CH2CH2 n-C4H9 S-239 O H H CH2CH2 iso-C4H9 S-240 O HH CH2CH2 sec-C4H9 S-241 O H H CH2CH2 tert-C4H9 S-242 O H H CH2CH2n-C5H11 S-243 O H H CH2CH2 n-C6H13 S-244 O H H CH2CH2 cyclo-C3H5 S-245 OH H CH2CH2 cyclo-C5H9 S-246 O H H CH2CH2 cyclo-C6H11 S-247 O H H CH2CH2CH2═CHCH2 S-248 O H H CH2CH2 CHCCH2 S-249 O H H CH2CH2 PhCH2 S-250 O H HCH2CH2 Ph(CH3)CH S-251 O H H CH2CH2 Ph(CH3)2C S-252 O H H CH2CH2 PhS-253 O H H CH2CH2 2-Cl—Ph S-254 O H H CH2CH2 3-Cl—Ph S-255 O H H CH2CH24-Cl—Ph S-256 O H H CH2CH2 4-CF3O—Ph S-257 O H H CH2CH2 4-(4-CF3—PhO)—PhS-258 O CH3 H CH2CH2 CH3 S-259 O CH3 H CH2CH2 C2H5 S-260 O CH3 H CH2CH2n-C3H7 S-261 O CH3 H CH2CH2 iso-C3H7 S-262 O CH3 H CH2CH2 n-C4H9 S-263 OCH3 H CH2CH2 iso-C4H9 S-264 O CH3 H CH2CH2 sec-C4H9 S-265 O CH3 H CH2CH2tert-C4H9 S-266 O CH3 H CH2CH2 n-C5H11 S-267 O CH3 H CH2CH2 n-C6H13S-268 O CH3 H CH2CH2 cyclo-C3H5 S-269 O CH3 H CH2CH2 cyclo-C5H9 S-270 OCH3 H CH2CH2 cyclo-C6H11 S-271 O CH3 H CH2CH2 CH2═CHCH2 S-272 O CH3 HCH2CH2 CHCCH2 S-273 O CH3 H CH2CH2 PhCH2 S-274 O CH3 H CH2CH2 Ph(CH3)CHS-275 O CH3 H CH2CH2 Ph(CH3)2C S-276 O CH3 H CH2CH2 Ph S-277 O CH3 HCH2CH2 2-Cl—Ph S-278 O CH3 H CH2CH2 3-Cl—Ph S-279 O CH3 H CH2CH2 4-Cl—PhS-280 O CH3 H CH2CH2 4-CF3O—Ph S-281 O CH3 H CH2CH2 4-(4-CF3—PhO)—PhS-282 O CH3 CH3 CH2CH2 H S-283 O CH3 CH3 CH2CH2 CH3 S-284 O CH3 CH3CH2CH2 C2H5 S-285 O CH3 CH3 CH2CH2 n-C3H7 S-286 O CH3 CH3 CH2CH2iso-C3H7 S-287 O CH3 CH3 CH2CH2 n-C4H9 S-288 O CH3 CH3 CH2CH2 iso-C4H9S-289 O CH3 CH3 CH2CH2 sec-C4H9 S-290 O CH3 CH3 CH2CH2 tert-C4H9 S-291 OCH3 CH3 CH2CH2 n-C5H11 S-292 O CH3 CH3 CH2CH2 n-C6H13 S-293 O CH3 CH3CH2CH2 cyclo-C3H5 S-294 O CH3 CH3 CH2CH2 cyclo-C5H9 S-295 O CH3 CH3CH2CH2 cyclo-C6H11 S-296 O CH3 CH3 CH2CH2 CH2═CHCH2 S-297 O CH3 CH3CH2CH2 CHCCH2 S-298 O CH3 CH3 CH2CH2 PhCH2 S-299 O CH3 CH3 CH2CH2Ph(CH3)CH S-300 O CH3 CH3 CH2CH2 Ph(CH3)2C S-301 O CH3 CH3 CH2CH2 PhS-302 O CH3 CH3 CH2CH2 2-Cl—Ph S-303 O CH3 CH3 CH2CH2 3-Cl—Ph S-304 OCH3 CH3 CH2CH2 4-Cl—Ph S-305 O CH3 CH3 CH2CH2 4-CF3O—Ph S-306 O CH3 CH3CH2CH2 4-(4-CF3—PhO)—Ph S-307 O OCH3 H CH2CH2 CH3 S-308 O OCH3 H CH2CH2C2H5 S-309 O OCH3 H CH2CH2 n-C3H7 S-310 O OCH3 H CH2CH2 iso-C3H7 S-311 OOCH3 H CH2CH2 n-C4H9 S-312 O OCH3 H CH2CH2 iso-C4H9 S-313 O OCH3 HCH2CH2 sec-C4H9 S-314 O OCH3 H CH2CH2 tert-C4H9 S-315 O OCH3 H CH2CH2n-C5H11 S-316 O OCH3 H CH2CH2 n-C6H13 S-317 O OCH3 H CH2CH2 cyclo-C3H5S-318 O OCH3 H CH2CH2 cyclo-C5H9 S-319 O OCH3 H CH2CH2 cyclo-C6H11 S-320O OCH3 H CH2CH2 CH2═CHCH2 S-321 O OCH3 H CH2CH2 CHCCH2 S-322 O OCH3 HCH2CH2 PhCH2 S-323 O OCH3 H CH2CH2 Ph(CH3)CH S-324 O OCH3 H CH2CH2Ph(CH3)2C S-325 O OCH3 H CH2CH2 Ph S-326 O OCH3 H CH2CH2 2-Cl—Ph S-327 OOCH3 H CH2CH2 3-Cl—Ph S-328 O OCH3 H CH2CH2 4-Cl—Ph S-329 O OCH3 HCH2CH2 4-CF3O—Ph S-330 O OCH3 H CH2CH2 4-(4-CF3—PhO)—Ph S-331 O OCH2CH3H CH2CH2 H S-332 O OCH2CH3 H CH2CH2 CH3 S-333 O OCH2CH3 H CH2CH2 C2H5S-334 O OCH2CH3 H CH2CH2 n-C3H7 S-335 O OCH2CH3 H CH2CH2 iso-C3H7 S-336O OCH2CH3 H CH2CH2 n-C4H9 S-337 O OCH2CH3 H CH2CH2 iso-C4H9 S-338 OOCH2CH3 H CH2CH2 sec-C4H9 S-339 O OCH2CH3 H CH2CH2 tert-C4H9 S-340 OOCH2CH3 H CH2CH2 n-C5H11 S-341 O OCH2CH3 H CH2CH2 n-C6H13 S-342 OOCH2CH3 H CH2CH2 cyclo-C3H5 S-343 O OCH2CH3 H CH2CH2 cyclo-C5H9 S-344 OOCH2CH3 H CH2CH2 cyclo-C6H11 S-345 O OCH2CH3 H CH2CH2 CH2═CHCH2 S-346 OOCH2CH3 H CH2CH2 CHCCH2 S-347 O OCH2CH3 H CH2CH2 PhCH2 S-348 O OCH2CH3 HCH2CH2 Ph(CH3)CH S-349 O OCH2CH3 H CH2CH2 Ph(CH3)2C S-350 O OCH2CH3 HCH2CH2 Ph S-351 O OCH2CH3 H CH2CH2 2-Cl—Ph S-352 O OCH2CH3 H CH2CH23-Cl—Ph S-353 O OCH2CH3 H CH2CH2 4-Cl—Ph S-354 O OCH2CH3 H CH2CH24-CF3O—Ph S-355 O OCH2CH3 H CH2CH2 4-(4-CF3—PhO)—Ph S-356 S H H CH2 HS-357 S H H CH2 n-C3H7 S-358 S H H CH2 iso-C3H7 S-359 S H H CH2 n-C4H9S-360 S H H CH2 iso-C4H9 S-361 S H H CH2 sec-C4H9 S-362 S H H CH2tert-C4H9 S-363 S H H CH2 n-C5H11 S-364 S H H CH2 n-C6H13 S-365 S H HCH2 cyclo-C3H5 S-366 S H H CH2 cyclo-C5H9 S-367 S H H CH2 cyclo-C6H11S-368 S H H CH2 CH2═CHCH2 S-369 S H H CH2 CHCCH2 S-370 S H H CH2 PhCH2S-371 S H H CH2 Ph(CH3)CH S-372 S H H CH2 Ph(CH3)2C S-373 S H H CH2 PhS-374 S H H CH2 2-Cl—Ph S-375 S H H CH2 3-Cl—Ph S-376 S H H CH2 4-Cl—PhS-377 S H H CH2 4-CF3O—Ph S-378 S H H CH2 4-(4-CF3—PhO)—Ph S-379 S CH3 HCH2 C2H5 S-380 S CH3 H CH2 n-C3H7 S-381 S CH3 H CH2 iso-C3H7 S-382 S CH3H CH2 n-C4H9 S-383 S CH3 H CH2 iso-C4H9 S-384 S CH3 H CH2 sec-C4H9 S-385S CH3 H CH2 tert-C4H9 S-386 S CH3 H CH2 n-C5H11 S-387 S CH3 H CH2n-C6H13 S-388 S CH3 H CH2 cyclo-C3H5 S-389 S CH3 H CH2 cyclo-C5H9 S-390S CH3 H CH2 cyclo-C6H11 S-391 S CH3 H CH2 CH2═CHCH2 S-392 S CH3 H CH2CHCCH2 S-393 S CH3 H CH2 PhCH2 S-394 S CH3 H CH2 Ph(CH3)CH S-395 S CH3 HCH2 Ph(CH3)2C S-396 S CH3 H CH2 Ph S-397 S CH3 H CH2 2-Cl—Ph S-398 S CH3H CH2 3-Cl—Ph S-399 S CH3 H CH2 4-Cl—Ph S-400 S CH3 H CH2 4-CF3O—PhS-401 5 CH3 H CH2 4-(4-CF3—PhO)—Ph S-402 S CH3 CH3 CH2 CH3 S-403 S CH3CH3 CH2 C2H5 S-404 S CH3 CH3 CH2 n-C3H7 S-405 S CH3 CH3 CH2 iso-C3H7S-406 S CH3 CH3 CH2 n-C4H9 S-407 S CH3 CH3 CH2 iso-C4H9 S-408 S CH3 CH3CH2 sec-C4H9 S-409 S CH3 CH3 CH2 tert-C4H9 S-410 S CH3 CH3 CH2 n-C5H11S-411 S CH3 CH3 CH2 n-C6H13 S-412 S CH3 CH3 CH2 cyclo-C3H5 S-413 S CH3CH3 CH2 cyclo-C5H9 S-414 S CH3 CH3 CH2 cyclo-C6H11 S-415 S CH3 CH3 CH2CH2═CHCH2 S-416 S CH3 CH3 CH2 CHCCH2 S-417 S CH3 CH3 CH2 PhCH2 S-418 SCH3 CH3 CH2 Ph(CH3)CH S-419 S CH3 CH3 CH2 Ph(CH3)2C S-420 S CH3 CH3 CH2Ph S-421 S CH3 CH3 CH2 2-Cl—Ph S-422 S CH3 CH3 CH2 3-Cl—Ph S-423 S CH3CH3 CH2 4-Cl—Ph S-424 S CH3 CH3 CH2 4-CF3O—Ph S-425 S CH3 CH3 CH24-(4-CF3—PhO)—Ph S-426 S OCH3 H CH2 C2H5 S-427 S OCH3 H CH2 n-C3H7 S-428S OCH3 H CH2 iso-C3H7 S-429 S OCH3 H CH2 n-C4H9 S-430 S OCH3 H CH2iso-C4H9 S-431 S OCH3 H CH2 sec-C4H9 S-432 S OCH3 H CH2 tert-C4H9 S-433S OCH3 H CH2 n-C5H11 S-434 S OCH3 H CH2 n-C6H13 S-435 S OCH3 H CH2cyclo-C3H5 S-436 S OCH3 H CH2 cyclo-C5H9 S-437 S OCH3 H CH2 cyclo-C6H11S-438 S OCH3 H CH2 CH2═CHCH2 S-439 S OCH3 H CH2 CHCCH2 S-440 S OCH3 HCH2 PhCH2 S-441 S OCH3 H CH2 Ph(CH3)CH S-442 S OCH3 H CH2 Ph(CH3)2CS-443 S OCH3 H CH2 Ph S-444 S OCH3 H CH2 2-Cl—Ph S-445 S OCH3 H CH23-Cl—Ph S-446 S OCH3 H CH2 4-Cl—Ph S-447 S OCH3 H CH2 4-CF3O—Ph S-448 SOCH3 H CH2 4-(4-CF3—PhO)—Ph S-449 S H H CH2CH2 C2H5 S-450 S H H CH2CH2n-C3H7 S-451 S H H CH2CH2 iso-C3H7 S-452 S H H CH2CH2 n-C4H9 S-453 S H HCH2CH2 iso-C4H9 S-454 S H H CH2CH2 sec-C4H9 S-455 S H H CH2CH2 tert-C4H9S-456 S H H CH2CH2 n-C5H11 S-457 S H H CH2CH2 n-C6H13 S-458 S H H CH2CH2cyclo-C3H5 S-459 S H H CH2CH2 cyclo-C5H9 S-460 S H H CH2CH2 cyclo-C6H11S-461 S H H CH2CH2 CH2═CHCH2 S-462 S H H CH2CH2 CHCCH2 S-463 S H HCH2CH2 PhCH2 S-464 S H H CH2CH2 Ph(CH3)CH S-465 S H H CH2CH2 Ph(CH3)2CS-466 S H H CH2CH2 Ph S-467 S H H CH2CH2 2-Cl—Ph S-468 S H H CH2CH23-Cl—Ph S-469 S H H CH2CH2 4-Cl—Ph S-470 S H H CH2CH2 4-CF3O—Ph S-471 SH H CH2CH2 4-(4-CF3—PhO)—Ph S-472 S CH3 H CH2CH2 CH3 S-473 S CH3 HCH2CH2 C2H5 S-474 S CH3 H CH2CH2 n-C3H7 S-475 S CH3 H CH2CH2 iso-C3H7S-476 S CH3 H CH2CH2 n-C4H9 S-477 S CH3 H CH2CH2 iso-C4H9 S-478 S CH3 HCH2CH2 sec-C4H9 S-479 S CH3 H CH2CH2 tert-C4H9 S-480 S CH3 H CH2CH2n-C5H11 S-481 S CH3 H CH2CH2 n-C6H13 S-482 S CH3 H CH2CH2 cyclo-C3H5S-483 S CH3 H CH2CH2 cyclo-C5H9 S-484 S CH3 H CH2CH2 cyclo-C6H11 S-485 SCH3 H CH2CH2 CH2═CHCH2 S-486 S CH3 H CH2CH2 CHCCH2 S-487 S CH3 H CH2CH2PhCH2 S-488 S CH3 H CH2CH2 Ph(CH3)CH S-489 S CH3 H CH2CH2 Ph(CH3)2CS-490 S CH3 H CH2CH2 Ph S-491 S CH3 H CH2CH2 2-Cl—Ph S-492 S CH3 HCH2CH2 3-Cl—Ph S-493 S CH3 H CH2CH2 4-Cl—Ph S-494 S CH3 H CH2CH24-CF3O—Ph S-495 S CH3 H CH2CH2 4-(4-CF3—PhO)—Ph S-496 S CH3 CH3 CH2CH2 HS-497 S CH3 CH3 CH2CH2 CH3 S-498 S CH3 CH3 CH2CH2 C2H5 S-499 S CH3 CH3CH2CH2 n-C3H7 S-500 S CH3 CH3 CH2CH2 iso-C3H7 S-501 S CH3 CH3 CH2CH2n-C4H9 S-502 S CH3 CH3 CH2CH2 iso-C4H9 S-503 S CH3 CH3 CH2CH2 sec-C4H9S-504 S CH3 CH3 CH2CH2 n-C4H9 S-505 S CH3 CH3 CH2CH2 iso-C4H9 S-506 SCH3 CH3 CH2CH2 seo-C4H9 S-507 S CH3 CH3 CH2CH2 tert-C4H9 S-508 S CH3 CH3CH2CH2 n-C5H11 S-509 S CH3 CH3 CH2CH2 n-C6H13 S-510 S CH3 CH3 CH2CH2cyclo-C3H5 S-511 S CH3 CH3 CH2CH2 cyclo-C5H9 S-512 S CH3 CH3 CH2CH2cyclo-C6H11 S-513 S CH3 CH3 CH2CH2 CH2═CHCH2 S-514 S CH3 CH3 CH2CH2CHCCH2 S-515 S CH3 CH3 CH2CH2 PhCH2 S-516 S CH3 CH3 CH2CH2 Ph(CH3)CHS-517 S CH3 CH3 CH2CH2 Ph(CH3)2C S-518 S CH3 CH3 CH2CH2 Ph S-519 S CH3CH3 CH2CH2 2-Cl—Ph S-520 S CH3 CH3 CH2CH2 3-Cl—Ph S-521 S CH3 CH3 CH2CH24-Cl—Ph S-522 S CH3 CH3 CH2CH2 4-CF3O—Ph S-523 S CH3 CH3 CH2CH24-(4-CF3—PhO)—Ph S-524 S OCH3 H CH2CH2 CH3 S-525 S OCH3 H CH2CH2 C2H5S-526 S OCH3 H CH2CH2 n-C3H7 S-527 S OCH3 H CH2CH2 iso-C3H7 S-528 S OCH3H CH2CH2 n-C4H9 S-529 S OCH3 H CH2CH2 iso-C4H9 S-530 S OCH3 H CH2CH2sec-C4H9 S-531 S OCH3 H CH2CH2 tert-C4H9 S-532 S OCH3 H CH2CH2 n-C5H11S-533 S OCH3 H CH2CH2 n-C6H13 S-534 S OCH3 H CH2CH2 cyclo-C3H5 S-535 SOCH3 H CH2CH2 cyclo-C5H9 S-536 S OCH3 H CH2CH2 cyclo-C6H11 S-537 S OCH3H CH2CH2 CH2═CHCH2 S-538 S OCH3 H CH2CH2 CHCCH2 S-539 S OCH3 H CH2CH2PhCH2 S-540 S OCH3 H CH2CH2 Ph(CH3)CH S-541 S OCH3 H CH2CH2 Ph(CH3)2CS-542 S OCH3 H CH2CH2 Ph S-543 S OCH3 H CH2CH2 2-Cl—Ph S-544 S OCH3 HCH2CH2 3-Cl—Ph S-545 S OCH3 H CH2CH2 4-Cl—Ph S-546 S OCH3 H CH2CH24-CF3O—Ph S-547 S OCH3 H CH2CH2 4-(4-CF3—PhO)—Ph S-548 O H H CH2 CH3OS-549 O H H CH2 PhCH2O S-550 O H H CH(CH3) H S-551 O H H CH(C2H5) HS-552 O H H CH(C2H5) PhCH2 S-553 O H H CHPh H S-554 O H H CHPh CH3 S-555O H H CHPh PhCH2 S-556 O CH3 H CH2 H S-557 O Ph H CH2 H S-558 O Ph H CH2CH3 S-559 O Ph H CH2 PhCH2

TABLE 5 Compounds of formula (IB): (1B)

Compound U X Y R⁴ T-1 O CH CH H T-2 O CH CH n-C3H7 T-3 O CH CH iso-C3H7T-4 O CH CH n-C4H9 T-5 O CH CH iso-C4H9 T-6 O CH CH sec-C4H9 T-7 O CH CHtert-C4H9 T-8 O CH CH n-C5H11 T-9 O CH CH n-C6H13 T-10 O CH CHcyclo-C3H5 T-11 O CH CH cycfo-C5H9 T-12 O CH CH cyclo-C6H11 T-13 O CH CHCH2═CHCH2 T-14 O CH CH CH2CCH T-15 O CH CH PhCH2 T-16 O CH CH Ph(CH3)OHT-17 O CH CH Ph T-18 O CH CH 2-Cl—Ph T-19 O CH CH 3-Cl—Ph T-20 O CH CH4-Cl—Ph T-21 O CH CH 4-CF3O—Ph T-22 O CH CH 4-(4-CF3—PhO)—Ph T-23 O CH NH T-24 O CH N CH3 T-25 O CH N n-C4H9 T-26 O CH N iso-C4H9 T-27 O CH Nsec-C4H9 T-28 O CH N tert-C4H9 T-29 O CH N n-C5H11 T-30 O CH N n-C6H13T-31 O CH N cyclo-C3H5 T-32 O CH N cyclo-C5H9 T-33 O CH N cyclo-C6H11T-34 O CH N CH2═CHCH2 T-35 O CH N CH2CCH T-36 O CH N PhCH2 T-37 O CH NPh(CH3)CH T-38 O CH N Ph T-39 O CH N 2-Cl—Ph T-40 O CH N 3-Cl—Ph T-41 OCH N 4-Cl—Ph T-42 O CH N 4-CF3O—Ph T-43 O CH N 4-(4-CF3—PhO)—Ph T-44 OCH N H T-45 O N N CH3 T-46 O N N C2H5 T-47 O N N n-C5H11 T-48 O N Nn-C6H13 T-49 O N N cyclo-C3H5 T-50 O N N cyclo-C5H9 T-51 O N Ncyclo-C6H11 T-52 O N N CH2═CHCH2 T-53 O N N CH2CCH T-54 O N N PhCH2 T-55O N N Ph(CH3)CH T-56 O N N Ph T-57 O N N 2-Cl—Ph T-58 O N N 3-Cl—Ph T-59O N N 4-Cl—Ph T-60 O N N 4-CF3O—Ph T-61 O N N 4-(4-CF3—PhO)—Ph T-62 S CHCH H T-63 S CH CH n-C3H7 T-64 S CH CH iso-C3H7 T-65 S CH CH n-C4H9 T-66S CH CH iso-C4H9 T-67 S CH CH sec-C4H9 T-68 S CH CH tert-C4H9 T-69 S CHCH n-C5H11 T-70 S CH CH n-C6H13 T-71 S CH CH cyclo-C3H5 T-72 S CH CHcyclo-C5H9 T-73 S CH CH cyclo-C6H11 T-74 S CH CH CH2═CHCH2 T-75 S CH CHCH2CCH T-76 S CH CH PhCH2 T-77 S CH CH Ph(CH3)CH T-78 S CH CH Ph T-79 SCH CH 2-Cl—Ph T-80 S CH CH 3-Cl—Ph T-81 S CH CH 4-Cl—Ph T-82 S CH CH4-CF3O—Ph T-83 S CH CH 4-(4-CF3—PhO)—Ph T-84 S CH N H T-85 S CH N CH3T-86 S CH N n-C4H9 T-87 S CH N iso-C4H9 T-88 S CH N sec-C4H9 T-89 S CH Ntert-C4H9 T-90 S CH N n-C5H11 T-91 S CH N n-C6H13 T-92 S CH N cyclo-C3H5T-93 S CH N cyclo-C5H9 T-94 S CH N cyclo-C6H11 T-95 S CH N CH2═CHCH2T-96 S CH N CH2CCH T-97 S CH N PhCH2 T-98 S CH N Ph(CH3)OH T-99 S CH NPh T-100 S CH N 2-Cl—Ph T-101 S CH N 3-Cl—Ph T-102 S CH N 4-Cl—Ph T-103S CH N 4-CF3O—Ph T-104 S CH N 4-(4-CF3—PhO)—Ph T-105 S N N H T-106 S N NCH3 T-107 S N N C2H5 T-108 S N N n-C5H11 T-109 S N N n-C6H13 T-110 S N Ncyclo-C3H5 T-111 S N N cyclo-C5H9 T-112 S N N cyclo-C6H11 T-113 S N NCH2═CHCH2 T-114 S N N CH2CCH T-115 S N N PhCH2 T-116 S N N Ph(CH3)CHT-117 S N N Ph T-118 S N N 2-Cl—Ph T-119 S N N 3-Cl—Ph T-120 S N N4-Cl—Ph T-121 S N N 4-CF3O—Ph T-122 S N N 4-(4-CF3—PhO)—Ph T-123 S N NPh

TABLE 6 Compounds of formula (IC): (1C)

Compound U R⁴ R⁹ R¹⁰ U-1 O H H H U-2 O n-C3H7 H H U-3 O iso-C3H7 H H U-4O n-C4H9 H H U-5 O iso-C4H9 H H U-6 O sec-C4H9 H H U-7 O tert-C4H9 H HU-8 O n-C5H11 H H U-9 O n-C6H13 H H U-10 O cyclo-C3H5 H H U-11 Ocyclo-C5H9 H H U-12 O cyclo-C6H11 H H U-13 O CH2CH═CH2 H H U-14 OCH2C(CH3)═CH2 H H U-15 O CH(CH3)CH═CH2 H H U-16 O CH2CH═CHCH3 H H U-17 OCH2CCH H H U-18 O CH2CCCH3 H H U-19 O CH(CH3)CCH H H U-20 O PhCH2 H HU-21 O Ph(CH3)CH H H U-22 O Ph(CH3)2C H H U-23 O Ph H H U-24 O 2-Cl—Ph HH U-25 O 3-Cl—Ph H H U-26 O 4-Cl—Ph H H U-27 S H H H U-28 S n-C3H7 H HU-29 S iso-C3H7 H H U-30 S n-C4H9 H H U-31 S iso-C4H9 H H U-32 Ssec-C4H9 H H U-33 S tert-C4H9 H H U-34 S n-C5H11 H H U-35 S n-C6H13 H HU-36 S cyclo-C3H5 H H U-37 S cyclo-C5H9 H H U-38 S cyclo-C6H11 H H U-39S CH2CH═CH2 H H U-40 S CH2C(CH3)═CH2 H H U-41 S CH(CH3)CH═CH2 H H U-42 SCH2CH═CHCH3 H H U-43 S CH2CCH H H U-44 S CH2CCCH3 H H U-45 S CH(CH3)CCHH H U-46 S PhCH2 H H U-47 S Ph(CH3)CH H H U-48 S Ph(CH3)2C H H U-49 S PhH H U-50 S 2-Cl—Ph H H U-51 S 3-Cl—Ph H H U-52 S 4-Cl—Ph H H

TABLE 7 Compounds of formula (ID): (1D)

Compound U R⁴ R¹¹ V-1 O H H V-2 O CH3 H V-3 O C2H5 H V-4 O n-C3H7 H V-5O iso-C3H7 H V-6 O n-C4H9 H V-7 O iso-C4H9 H V-8 O sec-C4H9 H V-9 Otert-C4H9 H V-10 O n-C5H11 H V-11 O n-C6H13 H V-12 O cyclo-C3H5 H V-13 Ocyclo-C5H9 H V-14 O cyclo-C6H11 H V-15 O CH2CH═CH2 H V-16 OCH2C(CH3)═CH2 H V-17 O CH(CH3)CH═CH2 H V-18 O CH2CH═CHCH3 H V-19 OCH2CCH H V-20 O CH2CCCH3 H V-21 O CH(CH3)CCH H V-22 O PhCH2 H V-23 OPh(CH3)CH H V-24 O Ph(CH3)2C H V-25 O Ph H V-26 O 2-Cl—Ph H V-27 O3-Cl—Ph H V-28 O 4-Cl—Ph H V-29 S H H V-30 S CH3 H V-31 S C2H5 H V-32 Sn-C3H7 H V-33 S iso-C3H7 H V-34 S n-C4H9 H V-35 S iso-C4H9 H V-36 Ssec-C4H9 H V-37 S tert-C4H9 H V-38 S n-C5H11 H V-39 S n-C6H13 H V-40 Scyclo-C3H5 H V-41 S cyclo-C5H9 H V-42 S cyclo-C6H11 H V-43 S CH2CH═CH2 HV-44 S CH2C(CH3)═CH2 H V-45 S CH(CH3)CH═CH2 H V-46 S CH2CH═CHCH3 H V-47S CH2CCH H V-48 S CH2CCCH3 H V-49 S CH(CH3)CCH H V-50 S PhCH2 H V-51 SPh(CH3)CH H V-52 S Ph(CH3)2C H V-53 S Ph H V-54 S 2-Cl—Ph H V-55 S3-Cl—Ph H V-56 S 4-Cl—Ph H

TABLE 8 Compounds of formula (I) wherein R¹ is —C(═U)NR³R⁴, U is NR¹⁸and m is zero. Compound R³ R⁴ R² R¹⁸ W-1 CH3 H H H W-2 C2H5 H H H W-3n-C3H7 H H H W-4 iso-C3H7 H H H W-5 n-C4H9 H H H W-6 iso-C4H9 H H H W-7tert-C4H9 H H H W-8 n-C5H11 H H H W-9 (CH3)3CCH2 H H H W-10 n-C6H13 H HH W-11 CH2═CHCH2 H H H W-12 CHCCH2 H H H W-13 cyclo-C3H5 H H H W-14cyclo-C5H9 H H H W-15 cyclo-C6H11 H H H W-16 PhCH2 H H H W-17 PhCH(CH3)H H H W-18 CH3NH H H H W-19 C2H5NH H H H W-20 n-C3H7NH H H H W-21iso-C3H7NH H H H W-22 n-C4H9NH H H H W-23 tert-C4H9NH H H H W-24n-C5H11NH H H H W-25 n-C6H13NH H H H W-26 PhCH2NH H H H W-27 PhNH H H HW-28 Ph H H H W-29 2-F—Ph H H H W-30 3-F—Ph H H H W-31 4-F—Ph H H H W-322-Cl—Ph H H H W-33 3-Cl—Ph H H H W-34 4-Cl—Ph H H H W-35 2-CF3—Ph H H HW-36 3-CF3—Ph H H H W-37 4-CF3—Ph H H H W-38 2-CH3—Ph H H H W-393-CH3—Ph H H H W-40 4-CH3—Ph H H H W-41 2-CH3O—Ph H H H W-42 3-CH3O—Ph HH H W-43 4-CH3O—Ph H H H W-44 CF3CH2 H H H W-45 ClCH2CH2 H H H W-46ClCH2CH2CH2 H H H W-47 CH3OCH2CH2 H H H W-48 CH3CH2OCH2CH2 H H H W-49CH3OCH2CH2CH2 H H H W-50 C2H5OCH2CH2CH2 H H H W-51 n-C4H9OCH2CH2CH2 H HH W-52 CH3OCH(CH3)CH2CH2 H H H W-53 (CH3O)2CHCH2 H H H W-54 HOCH2CH2 H HH W-55 HOCH2CH2CH2 H H H W-56 CH3SCH2CH2 H H H W-57 CH3CH2SCH2CH2 H H HW-58 CH3SCH2CH2CH2 H H H W-59 C2H5SCH2CH2CH2 H H H W-60 CH2CH2CH2CH2 H HW-61 CH2CH2CH2CH2CH2 H H W-62 CH2CH2OCH2CH2 H H W-63 CH2CH2SCH2CH2 H HW-64 CH2CH2NHCH2CH2 H H W-65 CH2CH2N(CH3)CH2CH2 H H W-66 N═CHCH2CH2 H HW-67 N═CHCH═CH H H W-68 CH3 CH3 H H W-69 C2H5 CH3 H H W-70 n-C3H7 CH3 HH W-71 iso-C3H7 CH3 H H W-72 n-C4H9 CH3 H H W-73 iso-C4H9 CH3 H H W-74tert-C4H9 CH3 H H W-75 n-C5H11 CH3 H H W-76 n-C6H13 CH3 H H W-77CH2═CHCH2 CH3 H H W-78 CHCCH2 CH3 H H W-79 cyclo-C3H5 CH3 H H W-80cyclo-C5H9 CH3 H H W-81 cyclo-C6H11 CH3 H H W-82 PhCH2 CH3 H H W-83CH3NH CH3 H H W-84 C2H5NH CH3 H H W-85 n-C3H7NH CH3 H H W-86 iso-C3H7NHCH3 H H W-87 n-C4H9NH CH3 H H W-88 tert-C4H9NH CH3 H H W-89 n-C5H11NHCH3 H H W-90 n-C6H13NH CH3 H H W-91 PhCH2NH CH3 H H W-92 PhNH CH3 H HW-93 Ph CH3 H H W-94 2-F—Ph CH3 H H W-95 3-F—Ph CH3 H H W-96 4-F—Ph CH3H H W-97 2-Cl—Ph CH3 H H W-98 3-Cl—Ph CH3 H H W-99 4-Cl—Ph CH3 H H W-1002-CF3—Ph CH3 H H W-101 3-CF3—Ph CH3 H H W-102 4-CF3—Ph CH3 H H W-1032-CH3—Ph CH3 H H W-104 3-CH3—Ph CH3 H H W-105 4-CH3—Ph CH3 H H W-1062-CH3O—Ph CH3 H H W-107 3-CH3O—Ph CH3 H H W-108 4-CH3O—Ph CH3 H H W-109CF3CH2 CH3 H H W-110 ClCH2CH2 CH3 H H W-111 ClCH2CH2CH2 CH3 H H W-112CH3OCH2CH2 CH3 H H W-113 CH3CH2OCH2CH2 CH3 H H W-114 CH3OCH2CH2CH2 CH3 HH W-115 C2H5OCH2CH2CH2 CH3 H H W-116 n-C4H9OCH2CH2CH2 CH3 H H W-117CH3OCH(CH3)CH2CH2 CH3 H H W-118 (CH3O)2CHCH2 CH3 H H W-119 HOCH2CH2 CH3H H W-120 HOCH2CH2CH2 CH3 H H W-121 CH3 C2H5 H H W-122 C2H5 C2H5 H HW-123 n-C3H7 C2H5 H H W-124 iso-C3H7 C2H5 H H W-125 CH2═CHCH2 C2H5 H HW-126 CHCCH2 C2H5 H H W-127 cyclo-C3H5 C2H5 H H W-128 PhCH2 C2H5 H HW-129 CH3NH C2H5 H H W-130 C2H5NH C2H5 H H W-131 PhCH2NH C2H5 H H W-132PhNH C2H5 H H W-133 Ph C2H5 H H W-134 2-Cl—Ph C2H5 H H W-135 3-Cl—PhC2H5 H H W-136 4-Cl—Ph C2H5 H H W-137 2-CF3—Ph C2H5 H H W-138 3-CF3—PhC2H5 H H W-139 4-CF3—Ph C2H5 H H W-140 2-CH3O—Ph C2H5 H H W-1413-CH3O—Ph C2H5 H H W-142 4-CH3O—Ph C2H5 H H W-143 CF3CH2 C2H5 H H W-144ClCH2CH2 C2H5 H H W-145 ClCH2CH2CH2 C2H5 H H W-146 CH3OCH2CH2 C2H5 H HW-147 CH3CH2OCH2CH2 C2H5 H H W-148 CH3OCH2CH2CH2 C2H5 H H W-149C2H5OCH2CH2CH2 C2H5 H H W-150 n-C4H9OCH2CH2CH2 C2H5 H H W-151CH3OCH(CH3)CH2CH2 C2H5 H H W-152 (CH3O)2CHCH2 C2H5 H H W-153 HOCH2CH2C2H5 H H W-154 HOCH2CH2CH2 C2H5 H H W-155 CH3 H H CH3 W-156 C2H5 H H CH3W-157 n-C3H7 H H CH3 W-158 iso-C3H7 H H CH3 W-159 tert-C4H9 H H CH3W-160 CH2═CHCH2 H H CH3 W-161 CHCCH2 H H CH3 W-162 cyclo-C3H5 H H CH3W-163 PhCH2 H H CH3 W-164 CH3NH H H CH3 W-165 C2H5NH H H CH3 W-166n-C3H7NH H H CH3 W-167 iso-C3H7NH H H CH3 W-168 PhCH2NH H H CH3 W-169PhNH H H CH3 W-170 Ph H H CH3 W-171 2-Cl—Ph H H CH3 W-172 3-Cl—Ph H HCH3 W-173 4-Cl—Ph H H CH3 W-174 CH3OCH2CH2 H H CH3 W-175 CH3CH2OCH2CH2 HH CH3 W-176 CH3OCH2CH2CH2 H H CH3 W-177 C2H5OCH2CH2CH2 H H CH3 W-178n-C4H9OCH2CH2CH2 H H CH3 W-179 CH3OCH(CH3)CH2CH2 H H CH3 W-180(CH3O)2CHCH2 H H CH3 W-181 HOCH2CH2 H H CH3 W-182 HOCH2CH2CH2 H H CH3W-183 CH2CH2CH2CH2 H CH3 W-184 CH2CH2CH2CH2CH2 H CH3 W-185 CH2CH2OCH2CH2H CH3 W-186 CH2CH2SCH2CH2 H CH3 W-187 CH2CH2NHCH2CH2 H CH3 W-188CH2CH2N(CH3)CH2CH2 H CH3 W-189 N═CHCH2CH2 H CH3 W-190 CH3 H H tert-C4H9W-191 C2H5 H H tert-C4H9 W-192 n-C3H7 H H tert-C4H9 W-193 iso-C3H7 H Htert-C4H9 W-194 tert-C4H9 H H tert-C4H9 W-195 CH2═CHCH2 H H tert-C4H9W-196 CHCCH2 H H tert-C4H9 W-197 cyclo-C3H5 H H tert-C4H9 W-198 PhCH2 HH tert-C4H9 W-199 CH3NH H H tert-C4H9 W-200 PhCH2NH H H tert-C4H9 W-201PhNH H H tert-C4H9 W-202 Ph H H tert-C4H9 W-203 2-Cl—Ph H H tert-C4H9W-204 3-Cl—Ph H H tert-C4H9 W-205 4-Cl—Ph H H tert-C4H9 W-206 CH3OCH2CH2H H tert-C4H9 W-207 CH3CH2OCH2CH2 H H tert-C4H9 W-208 CH3OCH2CH2CH2 H Htert-C4H9 W-209 C2H5OCH2CH2CH2 H H tert-C4H9 W-210 (CH3O)2CHCH2 H Htert-C4H9 W-211 HOCH2CH2 H H tert-C4H9 W-212 HOCH2CH2CH2 H H tert-C4H9W-213 CH2CH2CH2CH2 H tert-C4H9 W-214 CH2CH2CH2CH2CH2 H tert-C4H9 W-215CH2CH2OCH2CH2 H tert-C4H9 W-216 CH2CH2SCH2CH2 H tert-C4H9 W-217CH2CH2NHCH2CH2 H tert-C4H9 W-218 CH2CH2N(CH3)CH2CH2 H tert-C4H9 W-219N═CHCH2CH2 H tert-C4H9 W-220 CH3 H H OH W-221 C2H5 H H OH W-222 n-C3H7 HH OH W-223 iso-C3H7 H H OH W-224 tert-C4H9 H H OH W-225 CH2═CHCH2 H H OHW-226 CHCCH2 H H OH W-227 cyclo-C3H5 H H OH W-228 PhCH2 H H OH W-229CH3NH H H OH W-230 C2H5NH H H OH W-231 PhCH2NH H H OH W-232 PhNH H H OHW-233 Ph H H OH W-234 2-Cl—Ph H H OH W-235 3-Cl—Ph H H OH W-236 4-Cl—PhH H OH W-237 CH3OCH2CH2 H H OH W-238 CH3CH2OCH2CH2 H H OH W-239CH3OCH2CH2CH2 H H OH W-240 C2H5OCH2CH2CH2 H H OH W-241 n-C4H9OCH2CH2CH2H H OH W-242 CH3OCH(CH3)CH2CH2 H H OH W-243 (CH3O)2CHCH2 H H OH W-244HOCH2CH2 H H OH W-245 HOCH2CH2CH2 H H OH W-246 CH2CH2CH2CH2 H OH W-247CH2CH2CH2CH2CH2 H OH W-248 CH2CH2OCH2CH2 H OH W-249 CH2CH2SCH2CH2 H OHW-250 CH2CH2NHCH2CH2 H OH W-251 CH2CH2N(CH3)CH2CH2 H OH W-252 N═CHCH2CH2H OH W-253 N═CHCH═CH H OH W-254 CH3 H H CH3O W-255 C2H5 H H CH3O W-256n-C3H7 H H CH3O W-257 iso-C3H7 H H CH3O W-258 tert-C4H9 H H CH3O W-259CH2═CHCH2 H H CH3O W-260 CHCCH2 H H CH3O W-261 cyclo-C3H5 H H CH3O W-262PhCH2 H H CH3O W-263 CH3NH H H CH3O W-264 C2H5NH H H CH3O W-265 PhCH2NHH H CH3O W-266 PhNH H H CH3O W-267 Ph H H CH3O W-268 2-Cl—Ph H H CH3OW-269 3-Cl—Ph H H CH3O W-270 4-Cl—Ph H H CH3O W-271 CH3OCH2CH2 H H CH3OW-272 CH3CH2OCH2CH2 H H CH3O W-273 CH3OCH2CH2CH2 H H CH3O W-274C2H5OCH2CH2CH2 H H CH3O W-275 n-C4H9OCH2CH2CH2 H H CH3O W-276CH3OCH(CH3)CH2CH2 H H CH3O W-277 (CH3O)2CHCH2 H H CH3O W-278 HOCH2CH2 HH CH3O W-279 HOCH2CH2CH2 H H CH3O W-280 CH3SCH2CH2 H H CH3O W-281CH3CH2SCH2CH2 H H CH3O W-282 CH3SCH2CH2CH2 H H CH3O W-283 C2H5SCH2CH2CH2H H CH3O

TABLE 9 Compounds of formula (I) wherein R¹ is —C(═V)OR^(3a) and m iszero. Compound V R^(3a) R² X-1 O cyclo-C3H5 H X-2 O cyclo-C5H9 H X-3 Ocyclo-C6H11 H X-4 O CH3NH H X-5 O C2H5NH H X-6 O n-C3H7NH H X-7 Oiso-C3H7NH H X-8 O n-C4H9NH H X-9 O tert-C4H9NH H X-10 O n-C5H11NH HX-11 O n-C6H13NH H X-12 O PhCH2NH H X-13 O PhNH H X-14 O CF3CH2 H X-15 OClCH2CH2 H X-16 O ClCH2CH2CH2 H X-17 O CH3OCH2CH2 H X-18 O CH3CH2OCH2CH2H X-19 O CH3OCH2CH2CH2 H X-20 O C2H5OCH2CH2CH2 H X-21 O n-C4H9OCH2CH2CH2H X-22 O CH3OCH(CH3)CH2CH2 H X-23 O (CH3O)2CHCH2 H X-24 O HOCH2CH2 HX-25 O HOCH2CH2CH2 H X-26 O CH3SCH2CH2 H X-27 O CH3CH2SCH2CH2 H X-28 OCH3SCH2CH2CH2 H X-29 O C2H5SCH2CH2CH2 H X-30 O CH3(cyclo-C3H5)CH H X-31O NCCH2CH2 H X-32 S cyclo-C3H5 H X-33 S cyclo-C5H9 H X-34 S cyclo-C6H11H X-35 S CH3NH H X-36 S C2H5NH H X-37 S n-C3H7NH H X-38 S iso-C3H7NH HX-39 S n-C4H9NH H X-40 S tert-C4H9NH H X-41 S n-C5H11NH H X-42 Sn-C6H13NH H X-43 S PhCH2NH H X-44 S PhNH H X-45 S CF3CH2 H X-46 SClCH2CH2 H X-47 S ClCH2CH2CH2 H X-48 S CH3OCH2CH2 H X-49 S CH3CH2OCH2CH2H X-50 S CH3OCH2CH2CH2 H X-51 S C2H5OCH2CH2CH2 H X-52 S n-C4H9OCH2CH2CH2H X-53 S CH3OCH(CH3)CH2CH2 H X-54 S (CH3O)2CHCH2 H X-55 S HOCH2CH2 HX-56 S HOCH2CH2CH2 H X-57 S CH3SCH2CH2 H X-58 S CH3CH2SCH2CH2 H X-59 SCH3SCH2CH2CH2 H X-60 S C2H5SCH2CH2CH2 H X-61 S CH3(cyclo-C3H5)CH H X-62S NCCH2CH2 H X-63 O cyclo-C3H5 CH3 X-64 O cyclo-C5H9 CH3 X-65 Ocyclo-C6H11 CH3 X-66 O CH3NH CH3 X-67 O C2H5NH CH3 X-68 O n-C3H7NH CH3X-69 O iso-C3H7NH CH3 X-70 O n-C4H9NH CH3 X-71 O tert-C4H9NH CH3 X-72 On-C5H11NH CH3 X-73 O n-C6H13NH CH3 X-74 O PhCH2NH CH3 X-75 O PhNH CH3X-76 O CF3CH2 CH3 X-77 O ClCH2CH2 CH3 X-78 O ClCH2CH2CH2 CH3 X-79 OCH3OCH2CH2 CH3 X-80 O CH3CH2OCH2CH2 CH3 X-81 O CH3OCH2CH2CH2 CH3 X-82 OC2H5OCH2CH2CH2 CH3 X-83 O n-C4H9OCH2CH2CH2 CH3 X-84 O CH3OCH(CH3)CH2CH2CH3 X-85 O (CH3O)2CHCH2 CH3 X-86 O HOCH2CH2 CH3 X-87 O HOCH2CH2CH2 CH3X-88 O CH3SCH2CH2 CH3 X-89 O CH3CH2SCH2CH2 CH3 X-90 O CH3SCH2CH2CH2 CH3X-91 O C2H5SCH2CH2CH2 CH3 X-92 O CH3(cyclo-C3H5)CH CH3 X-93 O NCCH2CH2CH3 X-94 S cyclo-C3H5 CH3 X-95 S cyclo-C5H9 CH3 X-96 S cyclo-C6H11 CH3X-97 S CH3NH CH3 X-98 S C2H5NH CH3 X-99 S n-C3H7NH CH3 X-100 Siso-C3H7NH CH3 X-101 S n-C4H9NH CH3 X-102 S tert-C4H9NH CH3 X-103 Sn-C5H11NH CH3 X-104 S n-C6H13NH CH3 X-105 S PhCH2NH CH3 X-106 S PhNH CH3X-107 S CF3CH2 CH3 X-108 S ClCH2CH2 CH3 X-109 S ClCH2CH2CH2 CH3 X-110 SCH3OCH2CH2 CH3 X-111 S CH3CH2OCH2CH2 CH3 X-112 S CH3OCH2CH2CH2 CH3 X-113S C2H5OCH2CH2CH2 CH3 X-114 S n-C4H9OCH2CH2CH2 CH3 X-115 SCH3OCH(CH3)CH2CH2 CH3 X-116 S (CH3O)2CHCH2 CH3 X-117 S HOCH2CH2 CH3X-118 S HOCH2CH2CH2 CH3 X-119 S CH3SCH2CH2 CH3 X-120 S CH3CH2SCH2CH2 CH3X-121 S CH3SCH2CH2CH2 CH3 X-122 S C2H5SCH2CH2CH2 CH3 X-123 SCH3(cyclo-C3H5)CH CH3 X-124 S NCCH2CH2 CH3 X-125 O cyclo-C3H5 C2H5 X-126O CH3NH C2H5 X-127 O C2H5NH C2H5 X-128 O n-C3H7NH C2H5 X-129 Oiso-C3H7NH C2H5 X-130 O n-C4H9NH C2H5 X-131 O tert-C4H9NH C2H5 X-132 OPhCH2NH C2H5 X-133 O PhNH C2H5 X-134 O CF3CH2 C2H5 X-135 O ClCH2CH2 C2H5X-136 O ClCH2CH2CH2 C2H5 X-137 O CH3OCH2CH2 C2H5 X-138 O CH3CH2OCH2CH2C2H5 X-139 O CH3OCH2CH2CH2 C2H5 X-140 O C2H5OCH2CH2CH2 C2H5 X-141 On-C4H9OCH2CH2CH2 C2H5 X-142 O CH3OCH(CH3)CH2CH2 C2H5 X-143 O(CH3O)2CHCH2 C2H5 X-144 O HOCH2CH2 C2H5 X-145 O HOCH2CH2CH2 C2H5 X-146 OCH3(cyclo-C3H5)CH C2H5 X-147 O NCCH2CH2 C2H5 X-148 S cyclo-C3H5 C2H5X-149 S CH3NH C2H5 X-150 S C2H5NH C2H5 X-151 S n-C3H7NH C2H5 X-152 Siso-C3H7NH C2H5 X-153 S n-C4H9NH C2H5 X-154 S tert-C4H9NH C2H5 X-155 SPhCH2NH C2H5 X-156 S PhNH C2H5 X-157 S CF3CH2 C2H5 X-158 S ClCH2CH2 C2H5X-159 S ClCH2CH2CH2 C2H5 X-160 S CH3OCH2CH2 C2H5 X-161 S CH3CH2OCH2CH2C2H5 X-162 S CH3OCH2CH2CH2 C2H5 X-163 S C2H5OCH2CH2CH2 C2H5 X-164 Sn-C4H9OCH2CH2CH2 C2H5 X-165 S CH3OCH(CH3)CH2CH2 C2H5 X-166 S(CH3O)2CHCH2 C2H5 X-167 S HOCH2CH2 C2H5 X-168 S HOCH2CH2CH2 C2H5 X-169 SCH3(cyclo-C3H5)CH C2H5 X-170 S NCCH2CH2 C2H5

TABLE 10 1H-NMR spectral details for representative Examples from theabove Tables. Nmr spectra were measured in deuterochloroform unlessotherwise stated. Cpd 1H-NMR A-2 3.7-3.9(2H, m), 5.1-5.2(2H, m),5.7-5.9(1H, m), 7.63(1H, d), 8.46(1H, brs), 8.83(1H, d), 8.91(1H, d),10.70(1H, brs) A-18 2.26(1H, t), 4.02(2H, dd), 7.66(1H, d), 8.34(1H,brs), 8.91(1H, s), 8.94(1H, d), 10.03(1H, brs) A-24 0.5-0.6(1H, m),0.7-0.8(1H, m), 2.6-2.7(1H, m), 7.65(1H, d), 8.33(1H, brs), 8.89(1H, s),8.93(1H, d), 9.68(1H, brs) A-26 9.83(1H, s), 8.93(1H, d), 8.89(1H, s),8.40(1H, d), 7.65(1H, d), 4.12(1H, dt), 2.27(2H, m), 1.98(2H, m),1.73(2H, m) A-28 1.4-2.0(4H, m), 3.8-4.1(1H, m), 7.64(1H, d), 8.28(1H,brd), 8.90(1H, s), 8.91(1H, d) A-30 1.2-1.4(5H, m), 1.5-1.9(5H, m),3.4-3.6(1H, m), 7.63(1H, d), 8.22(1H, brd), 8.89(1H, s), 8.91(1H, d)A-32 9.68(1H, s), 8.93(1H, d), 8.90(1H, s), 8.38(1H, t), 7.65(1H, d),3.10(2H, t), 1.00(1H, m), 0.53(2H, m), 0.22(1H, m) A-37 4.39(2H, d),7.1-7.4(5H, m), 7.62(1H, d), 8.69(1H, m), 8.7-9.0(3H, m) A-38 1.48(3H,d), 4.7-4.9(1H, m), 7.1-7.4(5H, m), 7.58(1H, d), 8.78(1H, brd), 8.86(1H,s), 8.90(1H, d) A-39 2.80(2H, t), 3.42(2H, t), 7.1-7.4(5H, m), 7.62(1H,d), 8.3-8.5(1H, m), 8.89(1H, s), 8.90(1H, d) A-62 3.80(3H, s), 4.31(1H,s), 6.86(2H, d), 7.16(2H, d), 7.62(1H, d), 8.62(1H, brs), 8.8-9.0(2H,m), 10.26(1H, s) A-64 3.83(3H, s), 7.66(1H, d), 8.89(1H, s), 8.94(1H,d), 9.21(1H, brs), 10.60(1H, brs) A-65 10.54(1H, s), 9.51(1H, s),8.94(1H, d), 8.89(1H, s), 7.65(1H, d)4.01(2H, q), 1.28(3H, t) A-6710.39(1H), 8.90-9.05(2H), 7.81(1H), 4.18(1H), 1.24(6H) A-71 1.35(9H, s),7.62(1H, d), 8.66(1H, s), 8.78(1H, d) A-74 10.58(1H, s), 10.04(1H, s),8.92(1H, d), 8.89(1H, s), 7.65(1H, d), 5.94(1H, m), 5.38(1H, d),5.35(1H, d), 4.39(2H, d) A-75 10.51(1H, brs), 8.94(1H, d), 8.89(1H, s),7.65(1H, d), 5.05(2H, S), 4.34(2H, s), 1.81(3H, s) A-79 10.45(1H, brs),8.96(1H, d), 8.88(1H, s), 8.52(1H, brs), 7.66(1H, d), 5.85(1H, m),5.67(1H, m), 4.38(2H, d), 1.77(3H, d) A-81 10.74(1H, brs), 9.37(1H,brs), 8.93(1H, d), 8.89(1H, s), 7.66(1H, d), 4.56(2H, s), 2.60(1H) A-851.33(3H, t), 4.29(2H, q), 4.48(2H, s), 7.64(1H, d), 8.85(1H, s),8.90(1H, d), 9.60(1H, brs), 11.11(1H, brs) A-86 4.92(2H, s), 7.3-7.5(5H,m), 7.63(1H, d), 8.8-9.0(2H, m), 9.91(1H, brs), 10.56(1H, brs) A-888.29(1H, d), 8.88(1H, s), 8.86(1H, s), 7.65(1H, d), 7.28(1H, t),6.93-6.99(3H) 4.93(2H, s), 3.83(3H, s) A-89 8.88(1H, s), 8.76(1H, d),8.63(1H, s), 7.55(1H, d), 7.36(2H, d), 6.88(2H, d), 4.99(2H, s),3.79(3H, s) A-90 8.97(1H, d), 8.93(1H, s), 8.52(1H, brs), 7.67(1H, d),7.35(2H, t), 7.11(2H, d), 7.10(1H, t) A-149 10.32(1H, s), 9.53(1H, s),8.98-9.01(2H), 7.68(1H, d), 7.44(2H, d), 7.33(2H, t), 7.15(1H, t) A-1537.0-7.1(1H, m), 7.2-7.3(1H, m), 7.3-7.5(1H, m), 7.68(1H, d), 7.9-8.1(1H,m), 8.9-9.1(2H, m), 9.82(1H, brs), 10.88(1H, brs) A-154 7.0-7.3(3H, m),7.51(1H, s), 7.71(1H, d), 8.99(1H, s), 9.03(1H, d), 10.21(1H, brs),10.46(1H, brs) A-155 7.2-7.3(2H, m), 7.4-7.5(2H, m), 7.69(1H, d),8.94(1H, s), 8.97(1H, d), 10.26(1H, brs), 10.42(1H, brs) A-1587.3-7.4(2H, m), 7.4-7.5(2H, m), 7.70(1H, d), 8.99(1H, s), 9.02(1H, d),9.30(1H, brs), 10.33(1H, brs) A-162 7.2-7.3(1H, m), 7.5-7.6(1H, m),7.6-7.7(2H, m), 7.93(1H, d), 8.96(1H, d), 8.98(1H, s), 9.68(1H, brs),10.72(1H, brs) A-170 3.82(3H, s), 6.8-6.9(2H, m), 7.3-7.5(2H, m),7.68(1H, d), 8.9-9.0(2H, m), 9.33(1H, brs), 10.17(1H, brs) A-1803.99(3H, s), 7.1-7.2(1H, m), 7.4-7.6(1H, m), 7.66(1H, d), 8.0-8.1(1H,m), 8.2-8.3(1H, m), 8.97(1H, d), 9.00(1H, s), 9.39(1H, brs), 12.32(1H,brs) A-190 10.42(1H, s), 9.11(1H, s), 9.01(1H, d), 7.86(1H, d), 7.60(1H,s), 7.53(1H, d), 7.31(1H, t), 7.11(1H, d), 4.62(2H) A-194 7.1-7.3(2H,m), 7.4-7.5(2H, m), 7.69(1H, d), 8.9-9.0(2H, m), 9.65(1H, brs),10.42(1H, brs) A-200 6.9-7.1(4H, m), 7.3-7.4(2H, m), 7.4-7.5(2H, m),7.69(1H, d), 8.9-9.0(2H, m), 9.34(1H, brs), 10.30(1H, brs) A-20310.38(1H, s), 9.58(1H, s), 8.98-9.01(2H), 7.71(1H, d), 7.59(2H, d),7.49(2H, d), 7.00-7.08(4H) A-204 7.2-7.4(2H, m), 7.70(1H, d),8.1-8.2(1H, m), 8.79(1H, brs), 8.9-9.1(2H, m), 10.92(1H, brs) A-2057.0-7.1(1H, m), 7.3-7.4(1H, m), 7.71(1H, d), 7.9-8.0(1H, m), 8.99(1H,s), 9.03(1H, d), 10.08(1H, bes), 11.05(1H, brs) A-206 7.2-7.3(2H, m),7.3-7.4(2H, m), 7.65(1H, d), 8.92(1H, d), 8.95(1H, s), 9.36(1H, brs),9.92(1H, brs) A-207 7.1-7.2(1H, m), 7.3-7.4(1H, m), 7.6-7.7(1H, m),7.72(1H, d), 8.99(1H, s), 9.03(1H, d), 10.21(1H, brs), 10.50(1H, brs)A-208 7.1-7.2(1H, m), 7.4-7.5(2H, m), 7.72(1H, d), 8.97(1H, s), 9.03(1H,d), 9.13(1H, brs), 10.45(1H, brs) A-209 9.07(1H, s), 8.97(1H, d),8.27(1H, d), 8.00(1H, brs), 7.81(1H, d), 7.74(1H, t), 7.09(1H, t) A-21010.44(1H, s), 9.33(1H, brs), 9.02(1H, d), 8.99(1H, s), 8.71(1H, S),8.40(1H, d), 7.98(1H, d), 7.71(1H, d), 7.32(1H, dd) A-211 10.57(1H, s),9.12(1H, s), 9.02(1H, d), 8.48(2H, d), 7.87(1H, d), 7.63(2H, d) A-21212.48(1H, brs), 9.63(1H, brs), 8.88(1H, d), 8.81(1H, s), 8.65(2H, d),7.61(1H, d), 7.07(1H, t) A-222 7.01(1H, d), 7.48(1H, d), 7.71(1H, d),8.98(1H, s), 9.01(1H, d), 9.92(1H, brs) A-223 7.72(1H, d), 8.33(1H, s),8.87(1H, s), 8.98(1H, s), 9.01(1H, d), 10.18(1H, brs) A-248 3.8-4.0(2H,m), 7.67(1H, d), 8.6-8.8(1H, m), 8.91(1H, s), 8.96(1H, s), 9.80(1H, brs)A-250 1.9-2.1(2H, m), 3.3-3.5(2H, m), 3.5-3.7(2H, m), 7.65(1H, d),8.43(1H, brs), 8.90(1H, s), 8.93(1H, d), 10.35(1H, brs) A-251 3.39(3H,s), 3.4-3.6(4H, m), 7.65(1H, d), 8.43(1H, brs), 8.90(1H, s), 8.94(1H,d), 9.02(1H, brs) A-255 0.92(3H, t), 1.3-1.5(2H, m), 1.5-1.7(2H, m),1.7-1.9(2H, m), 3.2-3.6(6H, m), 7.63(1H, d), 8.45(1H, brs), 8.89(1H, s),8.91(1H, d), 10.00(1H, brs) A-256 3.3-3.6(m, 8H), 4.44(1H, t), 7.65(1H,d), 8.40(1H, brs), 8.90(1H, s), 8.93(1H, s), 9.40(1H, brs) A-2603.4-3.5(2H, m), 3.7-3.9(2H, m), 7.67(1H, d), 8.58(1H, brs), 8.91(1H, s),8.95(1H, d), 9.22(1H, brs) A-261 10.89(1H, s), 8.89-8.93(2H), 8.55(1h,d), 7.66(1H, d), 3.32-3.64(4H), 1.71-1.76(2H) A-262 3.78(3H, s),3.98(2H, d), 7.64(1H, d), 8.7-8.9(1H, m), 8.89(1H, s), 8.92(1H, d),10.31(1H, brs) A-265 4.43(2H, d), 7.84(1H, d), 8.81(1H, brs), 9.00(1H,d), 9.08(1H, s) A-267 8.97(1H, d), 8.93(1H, s), 8.60(1H, s), 7.67(1H,d), 1.74(6H, s) A-268 1.0-1.2(6H, m), 1.61(3H, s), 2.1-2.3(1H, m),7.66(1H, d), 8.73(1H, brs), 8.94(1H, s), 8.96(1H, d), 10.05(1H, brs)A-274 1.5-1.7(4H, m), 2.3-2.6(6H, m), 3.2-3.4(2H, m), 7.62(1H, d),8.5-8.7(1H, m), 8.8-9.0(2H, m), 10.40(1H, brs) A-292 1.0-1.9(10H, m),2.88(3H, s), 3.7-4.0(1H, m), 7.55(1H, d), 8.74(1H, s), 8.82(1H, d) A-2962.98(3H, s), 4.52(2H, s), 7.2-7.4(5H, m), 7.57(1H, d), 8.52(1H, brs),8.74(1H, s), 8.34(1H, d) A-312 3.11(3H, s), 7.73(1H, d), 8.74(1H, s),8.87(1H, s), 9.39(1H, s), 9.79(1H, brs) A-313 3.13(3H, s), 3.79(3H, s),7.57(1H, d), 8.72(1H, s), 8.85(1H, d), 8.90(1H, brs) A-316 1.32(6H, d),3.12(3H, s), 4.1-4.3(1H, m), 7.56(1H, d), 8.70(1H, s), 8.78(1H, brs),8.84(1H, d) A-317 3.17(3H, s), 4.40(2H, d), 5.3-5.6(2H, m), 5.9-6.1(1H,m), 7.57(1H, d), 8.68(1H, s), 8.84(1H, d) A-326 1.50(1H, s), 3.09(3H,s), 3.83(3H, s), 5.54(1H, q), 7.58(1H, d), 8.78(1H, s), 8.85(1H, d)A-329 3.13(3H, s), 4.88(2H, s), 7.3-7.5(5H, m), 7.53(1H, d), 8.43(1H,s), 8.59(1H, brs), 8.82(1H, d) A-331 3.17(3H, s), 7.81(1H, d), 8.96(1H,d), 9.13(1H, s), 10.22(1H, brs) A-349 8.84(1H, d), 8.69(1H, s), 7.69(1H,brs), 7.50-7.59(4H), 7.29(2H, d), 3.21(3H, s) A-353 8.84(1H, d),8.70(1H, s), 7.55-7.62(2H), 7.24-7.46(3H), 3.16(3H, s) A-354 8.84(1H,d), 8.70(1H, s), 7.57(1H, d), 7.45-7.48(2H), 7.32(1H), 7.20(1H),3.21(3H, s) A-355 8.84(1H, d), 8.69(1H, s), 7.57(1H, s), 7.50(2H, d),7.24(2H, d), 3.20(3H, s) A-365 8.84(1H, d), 8.67(1H, s), 7.55-7.58(2H),7.27-7.39(2H), 7.22(1H, d), 3.13(3H, s), 2.30(3H, s) A-366 8.82(1H, d),8.67(1H, s), 7.77(1H, s), 7.56(1H, d), 7.38(1H, t), 7.23(1H,d)7.06-7.10(2H), 3.18(3H, s), 2.41(3H, s) A-367 8.84(1H, d), 8.68(1H,s), 7.61(1H, s), 7.56(1H, d), 7.30(2H, d), 7.16(2H, d), 3.18(3H, s),2.42(3H, s) A-369 8.80(1H, d)8.66(1H, s), 7.91(1H, s), 7.55(1H, d),7.39(1H, t), 6.93(1H, dd), 6.86(1H, d), 6.79(1H, d), 3.83(3H, s),3.19(3H, s) A-373 8.89(1H, d), 8.85(1H, s), 8.29(2H, d), 7.80(1H, d),7.73(2H, d), 3.41(3H, s) A-381 8.86(1H, d), 8.73(1H, s), 7.73(1H, d)7.29(1H, t), 6.83-6.92(3H), 3.19(3H, s) A-398 13.93(1H, s), 8.84(1H, d),8.75(1H, s), 8.37(1H, d), 7.83(1H, t), 7.58(1H, d), 7.09-7.16(2H),3.36(3H, s) A-431 3.51(2H, t), 3.64(2H, t), 7.59(1H, d), 8.78(1H, s),8.82(1H, d), 10.38(1H, brs) A-519 1.11(3H, t), 3.2-3.4(2H, m),3.4-3.6(2H, m), 3.7-3.9(2H, m), 7.56(1H, d), 8.73(1H, s), 8.80(1H, d)A-524 0.85(3H, t), 1.4-1.7(2H, m), 3.1-3.3(2H, m), 3.4-3.6(2H, m),3.7-3.9(2H, m), 4.82(1H, brs), 7.56(1H, d), 8.72(1H, s), 8.78(1H, d),10.54(1H, brs) A-529 8.82(1H, d), 8.62(1H, s), 8.73(1H, brs), 7.54(1H,d), 7.25-7.60(5H), 4.40-4.58(3H), 1.16(6H) A-540 1.16(6H, d),4.2-4.5(1H, m), 7.63(1H, d), 8.68(1H, s), 8.82(1H, d), 9.02(1H, brs)A-544 8.84(1H, d), 8.69(1H, s), 7.56(1H, d), 4.10-4.25(2H), 1.34(3H, d),1.21(3H, d) A-564 8.82(1H, d), 8.67(1H, s), 7.50-7.57(3H),7.15-7.26(3H), 4.65(1H, m), 1.03(6H, d) A-605 1.10(6H, d), 3.3-3.5(2H,m), 3.8-4.0(2H, m), 4.3-4.5(1H, m), 7.54(1H, d), 8.79(1H, s), 8.80(1H,d) A-626 8.88(1H, d), 8.73(1H, s), 7.60(1H, d), 6.41(1H, brs), 1.17(9H,s) A-691 8.82(1H, d), 8.65(1H, s), 7.53(1H, d), 3.95(2H, t), 3.58(2H,t), 1.36(9H, s) A-697 8.82(1H, d), 8.75(1H, brs), 8.71(1H, s), 7.56(1H,s), 5.75(2H, m), 5.19-5.30(4H), 3.29(4H, d) A-713 8.97(1H, s), 8.84(1H,d), 8.73(1H, s), 7.57(1H, d), 5.79(1H, m), 5.26(1H, d), 5.24(1H, d),4.11(2H, d), 3.78(3H, s) A-736 8.83(1H, d), 8.69(1H, s), 7.45-7.58(5H),7.24-7.28(2H), 5.78(1H, m), 5.12(1H, d), 5.08(1H, d), 4.17(2H, d), A-7378.84(1H, d), 8.71(1H, s), 7.55-7.62(2H), 7.27-7.45(3H), 5.80(1H, m),5.09(1H, d), 5.06(1H, d), 4.49(1H, dd), 3.81(1H, dd) A-738 8.84(1H, d),8.70(1H, s), 7.57(1H, d), 7.43-7.45(2H), 7.24-7.28(1H9, 7.16(1H, dd),5.77(1H, m), 5.14(1H, d), 5.10(1H, d), 4.16(2H, d A-744 8.81(1H, d),8.69(1H, s), 7.68(1H, d), 7.34(1H, t), 6.88-6.95(3H), 5.77(1H, m),5.05(1H, d), 5.02(1H, d), 4.19(2H, d), 3.80(3H, s) A-745 8.83(1H, d),8.68(1H, s), 7.56(1H, d), 7.15(2H, d), 6.98(2H, d), 5.76(1H, m),5.10(1H, d), 5.06(1H, d), 4.12(2H, d), 3.86(3H, s) A-747 8.85(1H, d),8.70-8.721(2H), 7.72(1H, d), 7.28(1H, t), 6.82-6.89(3H), 5.82(1H, m),5.03-5.14(2H), 4.20(2H, d) A-748 8.80(!h, d), 8.68(1H, s), 7.84(1H, s),7.59(1H, d), 7.07(2H, d), 6.89(2H, d), 5.77(1H, m), 5.00-5.30(2H),4.11(2H, d) A-798 4.61(2H, s), 7.2-7.4(5H, m), 7.54(1H, d), 8.54(1H, s),8.62(1H, d), 9.18(1H, brs), 10.38(1H, brs) A-799 8.95(1H, s), 8.86(1H,d), 8.73(1H, s), 7.57(1H, d), 7.24-7.36(5H), 4.65(2H, s), 3.68(3H, s)A-805 8.80(1H, d), 8.45(1H, s), 7.53(1H, d), 7.23-7.41(10H), 4.75(2H,s), 4.64(2H, s) A-822 8.86(1H, d), 8.71(1H, s), 7.58(2H), 7.42(3H),7.24(3H), 7.04-7.11(4H), 4.76(2H, s) A-861 9.30(1H, s), 8.81(1H, d),8.73(1H, s), 7.55(1H, d), 4.38(1H, m), 3.83(1H, d), 3.03(1H, t),1.50-1.75(6H), 1.22(3H, d) A-862 3.3-3.5(2H, m), 3.6-3.8(2H, m),4.47(2H, s), 7.1-7.4(5H, m), 7.57(1H, d), 8.73(1H, s), 8.79(1H, d) A-8648.79(1H, d), 8.72(1H, s), 7.56(1H, d), 4.45(1H, brs), 3.20-3.80(4H),1.90-2.10(2H) A-865 8.84(1H, d), 8.74(1H, s), 8.42(1H, brs), 7.57(1H,d), 5.87(2H, brd), 4.33(2H, s), 4.18(2H, s) A-866 11.32(1H, brs),9.18(1H, s), 9.05(1H, d), 7.97(1H, d), 7.96(1H, d), 7.94(1H, d),7.47(1H, t), 7.33(1H, t) A-867 8.86(1H, d), 8.78(1H, s), 7.71(1H, d),7.25-7.45(10H) A-869 3.6-3.9(4H, m), 7.2-7.6(6H, m), 8.67(1H, d),8.79(1H, m) A-871 1.7-2.2(4H, m), 3.2-3.7(4H, m), 7.56(1H, d), 8.73(1H,s), 8.81(1H, d), 9.11(1H, brs) A-872 1.5-1.8(6H, m), 3.3-3.6(4H, m),7.56(1H, d), 8.75(1H, s), 8.83(1H, d), 8.93(brs) A-873 3.4-3.6(4H, m),3.6-3.9(4H, m), 7.58(1H, d), 8.03(1H, brs), 8.76(1H, s), 8.86(1H, d)A-874 2.6-2.8(4H, m), 4.7-4.9(4H, m), 7.59(1H, d), 8.77(1H, s), 8.86(1H,d) B-37 4.85(2H, d), 7.2-7.5(5H, m), 7.62(1H, d), 8.85(1H, s), 8.92(1H,d), 9.74(1H, brs), 10.61(1H, brs) B-40 10.83(1H, s), 8.95(1H, d),8.91(1H, s), 8.78(1H, s), 7.65(1H, d), 7.25-7.67(5H), 1.91(6H) B-4710.58(1H), 9.14(1H, s), 8.97(1H, d), 8.90(1H, s), 7.67(1H, d),7.24-7.38(4H), 4.86(2H, d) B-64 3.84(3H, s), 7.79(1H, s), 8.84(1H, s),8.93(1H, d), 10.78(1H, brs) B-65 12.41(1H, s), 10.66(1H, s), 8.93(1H,s), 8.87(1H, d), 7.70(1H, d), 4.07(2H, q), 1.16(3H, t) B-71 12.14(1H,s), 9.22(1H, s), 8.98(1H, d), 8.92(1H, s), 7.68(1H, d), 1.43(9H, s) B-7412.53(1H, s), 10.79(1H, s), 9.00(1H, s), 8.95(1H, d), 7.79(1H, d),6.02(1H, m), 5.38(1H, d), 5.28(1H, d), 4.60(2H, d) B-86 12.22(1H, s),9.22(1H, brs), 8.95(1H, d), 8.86(1H, s), 7.66(1H, d), 7.37-7.44(5H),5.14(2H, s) B-100 2.84(1H, brs), 3.36(1H, brs), 7.87(1H, d), 8.28(1H,brs), 9.03(1H, d), 9.17(1H, s) B-108 5.40(2H, s), 7.2-7.5(5H, m),7.71(1H, d), 8.9-9.1(2H, m), 12.80(1H, brs) B-109 6.8-7.1(4H, m),7.3-7.4(1H, m), 7.65(1H, d), 8.90(1H, s), 8.96(1H, d), 8.49(1H, brs),11.82(1H, d) B-149 12.34(1H, s), 10.95(1H, brs), 9.14(1H, s), 9.02(1H,d), 7.86(1H, d), 7.81(2H, d), 7.44(2H, t), 7.29(1H, m) B-150 12.35(1H,s), 11.15(1H, brs), 9.16(1H, s), 9.03(1H, d), 8.34(1H, t), 7.87(1H, d),7.25-7.35(3H) B-151 12.45(1H, s), 9.14(1H, s), 9.02(1H, d), 7.49(1H),7.47(1H, d), 7.46-7.50(2H), 7.07(1H, m) B-152 12.25(1H, s), 11.03(1H,brs), 9.12(1H, s), 9.02(1H, d), 7.86(1H, d), 7.78(2H, t), 7.21(2H, t)B-155 9.09(1H, s), 8.98(1H, d), 7.83(1H, d), 7.78(2H, d), 7.44(2H, d)B-158 9.13(1H, s), 9.02(1H, d), 7.87(1H, d), 7.79(2H, d), 7.62(2H, d)B-163 7.5-7.6(2H, m), 7.67(1H, d), 7.8-7.9(1H, m), 8.01(1H, d), 8.91(1H,s), 8.95(1H, s), 9.82(1H, brs), 12.25(1H, brs) B-166 9.00(1H, s),8.90(1H, d), 7.74(1H, d), 7.52(1H, d), 7.45(1H, s), 7.19(1H, t),6.99(1H, d), 2.25(3H, s) B-167 12.29(1H, s), 10.94(1H, brs), 9.13(1H,s), 9.01(1H, d), 7.86(1H, d), 7.66(2H, d), 7.25(2H, d), 2.34(3H, s)B-168 3.97(3H, s), 6.9-7.3(3H, m), 7.88(1H, d), 8.8-8.9(1H, m), 9.03(1H,d), 9.15(1H, s), 10.95(1H, brs), 12.73(1H, brs) B-169 3.83(3H, s),6.8-6.9(1H, m), 7.2-7.4(2H, m), 7.6-7.7(1H, m), 7.86(1H, d), 9.01(1H,d), 9.13(1H, s), 10.97(1H, brs), 12.38(1H, brs) B-170 3.79(3H, s),6.95(2H, d), 7.63(2H, d), 7.83(1H, d), 8.98(1H, d), 9.08(1H, s),10.93(1H, brs), 12.17(1H, brs) B-176 9.14(1H, s), 9.03(1H, d), 8.12(2H,d), 7.88(1H, d), 7.85(2H, d) B-184 12.35(1H, s), 10.96(1H, brs),9.13(1H, s), 9.02(1H, d), 8.58(1H, s), 7.86(1H, d), 7.53(1H, s),7.25(1H, t), 7.15(1H, t), 6.76(1H, d) B-185 12.14(1H, s), 10.92(1H,brs), 9.12(1H, s), 9.20(1H, d), 8.54(1H, brs), 7.85(1H, d), 7.56(2H, d),6.89(2H, d) B-189 4.71(2H, s), 7.2-7.4(2H, m), 7.5-7.6(1H, m),7.8-7.9(2H, m), 9.01(1H, d), 9.11(1H, s), 11.01(1H, brs), 12.13(1H, brs)B-190 12.38(1H, s), 10.98(1H), 9.15(1H, s), 9.03(1H, d), 7.87(1H, d),7.74(1H, d), 7.73(1H, s), 7.41(1H, t), 7.30(1H, d), 4.69(3H, s) B-19412.37(1H, brs), 9.13(1H, s), 9.03(1H, d), 7.92(2H, d), 7.87(1H, d),7.42(2H, d) B-209 9.99(1H, s), 9.18(1H, s), 9.04(1H, d), 8.48-8.55(3H),7.88(1H, d) B-247 7.5-8.0(6H, m), 8.99(1H, d), 9.01(1H, s), 10.64(1H,brs) B-251 3.42(3H, s), 3.65(2H, t), 3.8-4.0(2H, m), 7.66(1H, d),8.89(1H, s), 8.96(1H, d), 9.22(1H, brs), 10.48(1H, brs) B-255 0.91(3H,t), 1.3-1.5(2H, m), 1.5-1.7(2H, m), 1.9-2.1(2H, m), 3.46(3H, t),3.56(3H, t), 3.81(2H, q), 7.66(1H, d), 8.89(1H, s), 8.97(1H, d),9.02(1H, brs), 10.53(1H, brs) B-257 1.99(3H, s), 7.88(1H, d), 8.97(1H,d), 8.99(1H, s), 10.92(1H, brs), 12.92(1H, brs) B-258 7.5-7.7(3H, m),7.86(1H, s), 7.9-8.1(2H, m), 9.02(1H, d), 9.14(1H, brs) B-2597.3-7.5(5H, m), 7.5-7.7(5H, m), 7.77(1H, d), 8.8-9.0(2H, m), 13.05(1H,brs) B-261 1.8-2.0(2H, m), 3.76(2H, t), 3.8-3.9(2H, m), 7.66(1H, m),8.99(1H, s), 8.95(1H, d), 9.44(1H, brs), 10.53(1H, brs) B-267 9.08(1H,s), 9.01(1H, d), 7.84(1H, d), 1.95(6H, s) B-269 10.38(1H, brs), 9.35(1H,s), 8.96(1H, d), 8.90(1H, s), 7.67(1H, d), 3.73(4H), 1.60-1.80(4H) B-2963.23(3H, s), 5.22(2H, s), 7.22-7.5(5H, m), 7.63(1H, d), 8.7-9.0(2H, m)B-313 9.40(1H, s), 8.95(1H, d), 8.75(1H, s), 7.57(1H, d), 3.86(3H, s),3.58(3H, s) B-331 3.37(3H, s), 4.70(1H, s), 7.53(1H, d), 8.62(1H, s),8.80(1H, d) B-349 3.69(1H, s), 7.3-7.6(6H, m), 8.33(1H, brs), 8.51(1H,s), 8.79(1h, d) B-353 8.81(1H, d), 8.52(1H, s), 8.52(1H, s),7.53-7.60(2H), 7.25-7.46(3H), 3.62(3H, s) B-354 10.13(1H), 8.88(1H, d),8.48(1H, s), 7.72(1H, d), 7.37-7.55(4H), 3.75(3H, s) B-355 8.84(1H, d),8.57(1H, s), 8.15(1H, s), 7.56(1H, d), 7.43(2H, d), 7.27(2H, d),3.68(3H, s) B-366 8.81(1H, d), 8.58(1H, s), 8.14(1H, s), 7.54(1H, d),7.37(1H, d), 7.25(1H), 7.10(2H), 3.65(3H, s), 2.42(3H, s) B-369 8.47(1H,d), 8.03(1H, s), 7.33(1H, d), 7.02(1H, t), 6.54-6.64(3H), 3.45(3H, s),3.32(3H, s) B-373 8.87(1H, d), 8.62(1H, s), 8.35(1H, s9, 8.31(2H, d),7.57(1H, d), 7.53(2H, d), 3.78(3H, s) B-398 8.89(1H, d), 8.72(1H, s),8.51(1H, d), 7.98(1H, dd), 7.73(1H, d), 7.58(1H, d), 7.31(1H, dd),3.79(3H, s) B-417 9.15(1H, s), 8.88(1H, d), 7.69(1H, d), 4.16(3H, s),3.56(3H, s) B-431 3.38(3H, s), 3.7-4.2(4H, m), 7.5-7.7(1H, m),8.7-9.0(2H, m), 10.35(1H, brs) B-519 1.2-1.4(3H, m), 3.7-4.1(6H, m),7.56(1H, d), 8.6-9.0(2H, m), 10.85(1H, brs) B-564 9.08(1H, brs),8.36(1H, d), 7.51(1H, brs), 7.23(1H, d), 7.04-7.30(3H), 6.86-6.91(2H),5.17(1H), 0.74(6H, d) B-713 9.45(1H, s), 8.85(1H, d), 8.76(1H, s),7.56(1H, d), 5.90(1H, m), 5.27-5.36(2H), 4.70(2H, d), 3.86(3H, s) B-7368.85(1H, s) 8.27(1H, s), 7.69(1H, d), 7.30-7.50(5H), 6.10(1H, m),5.28(1H, d), 5.17(1H, d), 4.89(2H, d) B-737 8.83(1H, d), 8.12(1H, s),7.69(1H, d), 7.54-7.65(2H), 7.38-7.45(2H), 6.05(1H, m), 5.24(1H, d),5.21(1H, d), 5.00(1H, dd), 4.73(1H, dd) B-738 10.15(1H), 8.86(1H, d),8.40(1H, s), 7.71(1H, d), 7.35-7.54(4H), 6.00(1H, m), 5.27(1H, d),5.22(1H, d), 4.93(1H, d) B-744 8.80(1H, d), 8.59(1H, s), 8.11(1H, s),7.53(1H, d), 7.41(1H, t), 6.96(1H, dd), 6.84(1H, dd), 6.77(1H), 5.94(1H,m), 5.20(1H, d), 5.17(1H, d), 4.73(2H, d), 3.84(3H, s) B-745 8.80(1H,d), 8.67(1H, s), 8.13(1H, s), 7.53(1H, d), 7.17(2H, d), 6.98(2H, d),5.93(1H, m), 5.17(1H, d), 5.14(1H, d), 4.72(2H, d), 3.85(3H, s) B-7478.79(1H, d), 8.51(1H, s), 8.34(1H, s), 7.56(1H, d), 7.33(1H, t),7.26(1H, s), 6.87(1H, dd), 6.79(1H, dd), 6.74(1H, s), 5.91(1H, m),5.21(1H, d), 5.17(1H, d), 4.73(2H, d) B-748 9.69(1H, s), 8.80(1H, d),7.96(1H, s), 7.66(1H, d), 7.19(2H, d), 6.86(2H, d), 5.93(1H, m),5.12-5.25(2H), 4.89(2H, d) B-799 10.45(1H, brs), 8.90(1H, d), 8.86(1H,s), 7.76(1H, d), 7.30-7.46(5H), 5.41(2H, s), 3.88(3H, s) B-805 8.80(1H,d), 8.69(1H, s), 8.45(1H, s), 7.53(1H, d), 7.23-7.41(10H), 4.75(2H, s),4.64(2H, s) B-822 9.90(1H), 8.84(1H, d), 8.25(1H, s), 7.70(1H, d),7.24-7.45(10H), 5.62(2H, s) B-861 9.96(1H, brs), 8.95(1H, s), 8.93(1H,d), 7.79(1H, d), 5.40(1H, brs), 4.23(1H, brs), 3.34(1H) 1.60-1.94(6H),1.33(3H, d) B-863 8.86-8.95(2H), 7.65(1H, d), 5.62(1H), 3.85-4.35(4H),2.35-2.65(2H) B-864 8.93-8.98(2H), 7.79(1H, d), 4.75(1H), 3.70-4.00(4H),1.95-2.25(2H) B-865 8.93(2H), 8.42(1H, brs), 7.64(1H, d), 5.9(2H, m),4.64(2H, s), 4.57(2H, s) B-867 8.81(1H, d), 8.54(1H, s), 8.49(1H, s),7.54(1H, d), 7.28-7.45(10H) B-868 10.10(1H, s), 8.90(1H, d), 8.82(1H,s), 7.76(1H, d), 7.30-7.53(5H), 2.04(3H, s) B-870 10.38(1H,), 9.37(1H,s), 8.96(1H, d), 8.89(1H, s), 7.67(1H, d), 4.30(2H), 3.74(2H), 3.04(3H,s), 1.85-1.90(4H) B-871 1.9-2.2(4H, m), 3.7-4.0(4H, m), 7.62(1H, d),8.8-9.0(2H, m) B-872 1.6-1.9(6H, m), 3.6-3.8(2H, m), 4.0-4.3(2H, m),7.63(2h, d), 8.87(1H, brs), 8.9-9.0(2H, m) B-873 3.5-4.5(6H, m),7.64(1H, d), 8.56(1H, brs), 8.92(1H, s), 8.94(1H, d) B-874 8.94(1H, d),8.93(1H, s), 7.65(1H, d), 4.40(2H, brs), 4.02(2H, brs), 2.86(4H) B-8773.07(2H, dt), 3.96(2H, t), 7.06(1H, s), 7.74(1H, d), 8.73(1H, s),8.87(1H, d) B-880 1.87(6H, d), 7.2-7.8(6H, m), 8.77(1H, s), 8.83(1H, d)C-10 3.08(3H, s), 4.57(2H, s), 7.2-7.5(5H, m), 7.64(1H, d), 8.72(1H, s),8.89(1H, d), 9.34(1H, brs) C-78 3.10(3H, s), 3.26(3H, d), 4.5-4.8(2H,m), 7.1-7.5(5H, m), 7.64(1H, d), 8.72(1H, s), 8.90(1H, d), 9.34(1H, brs)C-85 3.02(3H, s), 3.34(3H, s), 3.64(3H, s), 7.58(1H, d), 8.65(1H, d),8.81(1H, d) C-91 2.88(3H, s), 2.98(3H, s), 4.72(2H, s), 7.30-7.43(5H),7.59(1H, d), 8.52(1H, s), 8.80(1H, d) D-85 1.33(1H, t), 2.98(3H, s),3.61(3H, s), 3.87(1H, q), 7.60(1H, d), 8.67(1H, s), 8.82(1H, d) D-861.2-1.4(6H, m), 3.7-4.0(4H, m), 7.59(1H, d), 8.67(1H, d), 8.81(1H, d)E-85 2.97(3H, s), 3.59(3H, s), 4.42(2H, d), 5.28(1H, d), 5.32(1H, d),5.98(1H, m), 7.61(1H, d), 8.68(1H, s), 8.83(1H, d) E-87 3.00(3H, s),4.25(2H, d), 4.37(2H, d), 5.2-5.5(4H, m), 5.7-6.1(2H, m), 7.61(1H, d),8.68(1H, s), 8.82(1H, d) F-85 2.35(1H, t), 3.09(3H, s), 3.68(3H, s),4.64(2H, d), 7.62(1H, d), 8.68(1H, s), 8.85(1H, d) F-88 2.37(1H, dd),2.62(1H, dd), 3.12(3H, s), 4.50(2H, d), 4.61(2H, d), 7.63(1H, d),8.73(1H, s), 8.86(1H, d) G-35 4.66(2H, s), 4.75(2H, s), 7.24-7.42(10H),7.43(1H, d), 8.46(1H, s), 8.83(1H, d) G-85 2.81(3H, s), 3.08(3H, s),5.06(2H, s), 7.26-7.32(3H), 7.45(2H, d), 7.59(1H, d), 8.70(1H, s),8.82(1H, d) G-91 2.71(3H, s), 4.29(2H, s), 4.71(2H, s), 7.0-7.1(2H, m),7.2-7.6(8H, m), 7.58(1H, d), 8.56(1H, s), 8.80(1H, d) G-126 4.31(2H, s),4.38(2H, s), 4.71(2H, s), 6.89(2H, d), 7.07(2H), 7.17-7.39(11H),7.50(1H, d), 8.39(1H, s), 8.58(1H, d) H-85 2.96(3H, s), 3.64(3H, s),3.81(3H, s), 4.59(2H, s), 7.62(1H, d), 8.80(1H, s), 8.85(1H, d) H-893.08(3H, S), 3.74(3H, s), 3.77(3H, s), 4.48(2H, s), 4.60(2H, s),7.64(1H, s), 8.84(1H, s), 8.87(1H, d) H-91 2.90(3H, s), 3.69(3H, s),4.76(2H, s), 7.24-7.45(5H), 7.64(1H, d), 8.80(1H, s), 8.85(1H, d) I-851.60(3H, d), 3.63(3H, s), 3.80(3H, s), 5.30(1H, q), 7.58(1H, d),8.78(1H, s), 8.84(1H, d) S-2 0.87(3H, t), 1.4-1.7(2H, m), 3.17(2H, t),3.54(2H, t), 4.06(2H, t), 7.54(1H, d), 8.65(1H, s), 8.81(1H, d) S-31.15(6H, d), 3.49(2H, t), 3.9-4.2(3H, m), 7.54(1H, d), 8.66(1H, s),8.81(1H, d) S-7 1.34(9H, s), 3.58(2H, t), 3.96(2H, t), 7.53(1h, d),8.65(1h, s), 8.81(1h, d) S-15 3.40(2H, t), 4.01(2H, t), 4.53(2H, s),7.1-7.4(5H, m), 7.57(1h, d), 8.69(1H, s), 8.83(1H, d) S-18 4.00(2H, t),4.18(2H, t), 7.1-7.5(5H, m), 7.57(1H, d), 8.70(1H, s), 8.83(1H, d) S-1091.25(3H, q), 3.1-3.3(1H, d), 3.4-3.6(1H, m), 3.7-4.0(2H, m), 4.28(1H,d), 4.47(1H, d), 5.76(1H, d), 7.1-7.5(5H, m), 7.57(1H, d), 8.70(1H, s),8.83(1H, d) S-120 1.37(6H, d), 4.2-4.4(1H, m), 4.42(2H, s), 7.62(1H, d),8.73(1H, s), 8.91(1H, d) S-124 1.55(9H, s), 4.34(2H, s), 7.60(1H, d),8.71(1H, s), 8.90(1H, d) S-132 4.47(2H, s), 4.62(2H, s), 7.2-7.4(4H, m),7.61(1H, d), 8.70(1H, s), 8.91(1H, d) S-143 1.36(6H, d), 1.70(3H, d),4.3-4.4(1H, m), 4.67(1H, q), 7.60(1H, d), 8.71(1H, s), 8.90(1H, d) S-1551.71(3H, d), 4.76(2H, s), 4.76(1H, q), 7.1-7.4(5H, m), 7.61(1H, d),8.69(1H, s), 8.91(1H, d) S-167 1.35(6H, d), 1.78(6H, s), 4.2-4.4(1H, m),7.58(1H, d), 8.67(1H, s), 8.88(1h, d) S-356 3.77(2H, t), 4.40(2H, t),6.81(1H, brs), 7.54(1H, d), 8.65(1H, s), 8.82(1H, d) S-357 0.94(3H, t),1.34(1h, m), 1.60(1H, m), 3.63(2H, t), 3.76(2H, t), 4.23(2H, t),7.51(1H, d), 8.62(1H, s), 8.79(1H, d) S-548 3.69(2H, t), 3.77(3h, s),4.00(2H, t), 7.57(1H, d), 8.67(1H, s), 8.86(1H, d) S-549 3.43(2H, t),3.88(2H, t), 4.90(2H, s), 7.30-7.40(5H), 7.57(1H, d), 8.67(1H, s),8.85(1H, d) S-550 1.40(3H, d), 4.09(1H, m), 4.34(1H, m), 4.64(1H, m),7.55(1H,, d), 8.78(1H, d), 9.14(1H, s), 9.47(1H, brs) S-551 1.03(3H, t),1.76(2H, m), 4.19(2H, m), 4.63(1H, m), 7.56(1H, d), 8.80(1H, d),9.17(1H, s), 9.49(1H, brs) S-552 0.88(3H, t), 1.80(2H, m), 3.82(1H, m),4.17(1H, d), 4.30(1H, dd), 4.63(1H, t), 5.12(1H, d), 7.23-7.38(5H),7.53(1H, d), 8.75(1H, d), 9.10(1H, s) S-553 4.38(1H, dd), 4.90(1H, t),5.27((1H), 7.25-7.53(5H), 7.57(1H, d), 8.81(1H, d), 9.22(1H, s),9.70(1H, brs) S-554 2.67(3H, s), 3.90(1H, dd), 4.45(1H, dd), 4.65(1h,dd), 7.30(2H), 7.40-7.450(3H), 7.60(1H, d), 8.73(1H, s), 8.87(1H, d)S-555 3.73(1H, d), 4.47(1H, t), 4.66(1H, t), 4.89(1H, t), 5.17(1H, d),7.10-7.46(10H), 7.57(1H, d), 8.79(1H, d), 9.18(1H, s) S-556 1.56(3H, d),3.51(1H, dd), 4.02(1h, t), 4.95(1H, m), 7.54(1H, d), 8.78(1H, d),9.15(1H, s), 9.32(1H, s) S-557 3.90(1H, t), 4.32(1H, t), 5.80(1H, t),7.38-7.46(5H), 7.57(1H, d), 8.81(1H, d), 9.21(1H, s), 9.42(1H, brs)S-558 3.08(3H, s), 3.60(1H, dd), 4.06(1H, t), 5.78(1H, dd),7.28-7.40(5H), 7.52(1H, d), 8.74(1H, d), 9.09(1H, s) S-559 3.44(1H, dd),3.89(1H, t), 4.60(1H, d), 4.73(1H, d), 5.76(1H, dd), 7.26-7.40(10H),7.53(1H, d9, 8.76(1H, d), 9.13(1H, s) U-3 8.80(1H, d), 8.66(1h, s),7.54(1H, d), 4.29(2H, t), 4.05(2H, t), 1.18(6H, d) U-7 8.78(1H, d),8.66(1H, s), 7.52(1H, d), 4.28(2H, t), 4.00(2H, t), 1.34(9H, s) U-208.81(1H, d), 8.67(1H, s), 7.55(1H, d), 7.25-7.50(5H), 4.66(2H, s),4.00-4.17(4H) W-194 1.45(18H, s), 7.54(1H, d), 7.75(1H, d), 9.08(1H, s),10.17(1H, brs) X-35 3.24(3H, d), 7.67(1H, d), 8.89(1H, s), 8.97(1H, d),9.24(1H, brs), 10.32(1H, brs) X-43 4.90(2H, d), 7.2-7.5(5H, m), 7.68(1H,d), 8.92(1H, s), 8.98(1H, d), 9.51(1H, brs), 10.62(1H, brs) X-459.00(1H, s), 8.97(1H, d), 7.82(1H, d), 5.04(2H, q) X-55 3.77(2H, t),4.55(2H, t), 7.64(1H, d), 8.84(1H, s), 8.92(1H, d), 9.27(1H, brs)

According to a further feature of the present invention there isprovided a method for the control of pests at a locus which comprisesthe application of an effective amount of a compound of formula (I) or asalt thereof. For this purpose, the said compound is normally used inthe form of a pesticidal composition (i.e. in association withcompatible diluents or carriers and/or surface active agents suitablefor use in pesticidal compositions), for example as hereinafterdescribed.

The term “compound of the invention” as used hereinafter embraces a3-pyridylcarboxamide of formula (I) as defined above and a pesticidallyacceptable salt thereof.

One aspect of the present invention as defined above is a method for thecontrol of pests at a locus. The locus includes, for example, the pestitself, the place (plant, field, forest, orchard, waterway, soil, plantproduct, or the like) where the pest resides or feeds, or a placesusceptible to future infestation by the pest. The compound of theinvention may therefore be applied directly to the pest, to the placewhere the pest resides or feeds, or to the place susceptible to futureinfestation by the pest.

As is evident from the foregoing pesticidal uses, the present inventionprovides pesticidally active compounds and methods of use of saidcompounds for the control of a number of pest species which includes:arthropods, especially insects or mites, or plant nematodes. Thecompound of the invention may thus be advantageously employed inpractical uses, for example, in agricultural or horticultural crops, inforestry, in veterinary medicine or livestock husbandry, or in publichealth.

The compounds of the invention may be used for example in the followingapplications and on the following pests:

For the control of soil insects, such as corn rootworm, termites(especially for protection of structures), root maggots, wireworms, rootweevils, stalkborers, cutworms, root aphids, or grubs. They may also beused to provide activity against plant pathogenic nematodes, such asroot-knot, cyst, dagger, lesion, or stem or bulb nematodes, or againstmites. For the control of soil pests, for example corn rootworm, thecompounds are advantageously applied to or incorporated at an effectiverate into the soil in which crops are planted or to be planted or to theseeds or growing plant roots.

In the area of public health, the compounds are especially useful in thecontrol of many insects, especially filth flies or other Dipteran pests,such as houseflies, stableflies, soldierflies, hornflies, deerflies,horseflies, midges, punkies, blackflies, or mosquitoes.

In the protection of stored products, for example cereals, includinggrain or flour, groundnuts, animal feedstuffs, timber or householdgoods, e.g. carpets and textiles, compounds of the invention are usefulagainst attack by arthropods, more especially beetles, includingweevils, moths or mites, for example Ephestia spp. (flour moths),Anthrenus spp. (carpet beetles), Tribolium spp. (flour beetles),Sitophilus spp. (grain weevils) or Acarus spp. (mites).

In the control of cockroaches, ants or termites or similar arthropodpests in infested domestic or industrial premises or in the control ofmosquito larvae in waterways, wells, reservoirs or other running orstanding water.

For the treatment of foundations, structures or soil in the preventionof the attack on building by termites, for example, Reticulitermes spp.,Heterotermes spp., Coptotermes spp.

In agriculture against adults, larvae and eggs of Lepidoptera(butterflies and moths), e.g. Heliothis spp. such as Heliothis virescens(tobacco budworm), Heliothis armigera and Heliothis zea. Against adultsand larvae of Coleoptera (beetles) e.g. Anthonomus spp. e.g. grandis(cotton boll weevil), Leptinotarsa decemlineata (Colorado potatobeetle), Diabrotica spp. (corn rootworms). Against Heteroptera(Hemiptera and Homoptera) e.g. Psylla spp., Bemisia spp., Trialeurodesspp., Aphis spp., Myzus spp., Megoura viciae, Phylloxera spp.,Nephotettix spp. (rice leaf hoppers), Nilaparvata spp.

Against Diptera e.g. Musca spp. Against Thysanoptera such as Thripstabaci. Against Orthoptera such as Locusta and Schistocerca spp.,(locusts and crickets) e.g. Gryllus spp., and Acheta spp. for example,Blatta orientalis, Periplaneta americana, Blatella germanica, Locustamigratoria migratorioides, and Schistocerca gregaria. Against Collembolae.g. Periplaneta spp. and Blatella spp. (roaches). Against arthropods ofagricultural significance such as Acari (mites) e.g, Acarus siro, Argasspp., Ornithodoros spp., Dermanyssus gallinae, Eriophyes ribis,Phyllocoptruta oleivora, Boophilus spp., Rhipicephalus spp., Amblyommaspp., Hyalomma spp., Ixodes spp., Psoroptes spp., Chorioptes spp.,Sarcoptes spp., Tarsonemus spp., Bryobia praetiosa, Panonychus spp.,Tetranychus spp., Eotetranychus spp., Oligonychus spp., Eutetranychusspp.

From the order of the Isopoda, for example, Oniscus aselus, Armadiumvulgare, Porcellio scaber.

Against nematodes which attack plants or trees of importance toagriculture, forestry or horticulture either directly or by spreadingbacterial, viral, mycoplasma or fungal diseases of the plants. Theplant-parasitic nematodes which can be controlled in accordance with theinvention include, for example, the root-parasitic soil-dwellingnematodes such as, for example, those of the genera Meloidogyne (rootknot nematodes, such as Meloidogyne incognita, Meloidogyne hapla andMeloidogyne javanica), Heterodera and Globodera (cyst-forming nematodes,such as Globodera rostochiensis, Globodera pallida, Heterodera trifolii)and of the genera Radopholus, such as Radopholus similis, Pratylenchussuch as Pratylenchus neglectus, Pratylenchus penetrans and Pratylenchuscurvitatus; Tylenchulus such as Tylenchulus semipenetrans,Tylenchorhynchus, such as Tylenchorhynchus dubius and Tylenchorhynchusclaytoni, Rotylenchus such as Rotylenchus robustus, Heliocotylenchussuch as Haliocotylenchus multicinctus, Belonoaimus such as Belonoaimuslongicaudatus, Longidorus such as Longidorus elongatus, Trichodorus suchas Trichodorus primitivus and Xiphinema such as Xiphinema index.

Other nematode genera which can be controlled using the compoundsaccording to the invention are Ditylenchus (stem parasites, such asDitylenchus dipsaci and Ditylenchus destructor), Aphelenchoides (foliarnematodes, such as Aphelenchoides ritzemabosi) and Anguina (seednematodes, such as Anguina tritici).

In the field of veterinary medicine or livestock husbandry or in themaintenance of public health against arthropods which are parasiticinternally or externally upon vertebrates, particularly warm-bloodedvertebrates, for example domestic animals, e.g. cattle, sheep, goats,equines, swine, poultry, dogs or cats, for example Acarina, includingticks (e.g. Ixodes spp., Boophilus spp. e.g. Boophilus microplus,Rhipicephalus spp. e.g. Rhipicephalus appendiculatus Ornithodorus spp.(e.g. Ornithodorus moubata) and mites (e.g. Damalinia spp.); fleas;Diptera (e.g. Aedes spp., Anopheles spp., Musca spp., Hypoderma spp.);Hemiptera; Dictyoptera (e.g. Periplaneta spp., Blatella spp.);Hymenoptera; for example against infections of the gastro-intestinaltract caused by parasitic nematode worms, for example members of thefamily Trichostrongylidae.

From the class of the helminths, for example, Haemonchus,Trichostrongulus, Ostertagia, Cooperia, Chabertia, Strongyloides,Oesophagostomum, Hyostrongulus, Ancylostoma, Ascaris and Heterakis andalso Fasciola.

From the class of the Gastropoda, for example, Deroceras spp., Arionspp., Lymnaea spp., Galba spp., Succinea spp., Biomphalaria spp.,Bulinus spp., Oncomelania spp.

From the class of the Bivalva, for example, Dreissena spp.

In practical use for the control of arthropods, especially insects oracarids, or nematode pests of plants, a method, for example, comprisesapplying to the plants or to the medium in which they grow an effectiveamount of a compound of the invention. For such a method, the compoundof the invention is generally applied to the locus in which thearthropod or nematode infestation is to be controlled at an effectiverate in the range of about 2 g to about 1 kg of the active compound perhectare of locus treated. Under ideal conditions, depending on the pestto be controlled, a lower rate may offer adequate protection. On theother hand, adverse weather conditions, resistance of the pest or otherfactors may require that the active ingredient be used at higher rates.The optimum rate depends usually upon a number of factors, for example,the type of pest being controlled, the type or the growth stage of theinfested plant, the row spacing or also the method of application.Preferably an effective rate range of the active compound is from about10 g/ha to about 400 g/ha, more preferably from about 50 g/ha to about200 g/ha.

When a pest is soil-borne, the active compound generally in a formulatedcomposition, is distributed evenly over the area to be treated (ie, forexample broadcast or band treatment) in any convenient manner and isapplied at rates from about 10 g/ha to about 400 g ai/ha, preferablyfrom about 50 g/ha to about 200 g ai/ha. When applied as a root dip toseedlings or drip irrigation to plants the liquid solution or suspensioncontains from about 0.075 to about 1000 mg ai/l, preferably from about25 to about 200 mg ai/l. Application may be made, if desired, to thefield or crop-growing area generally or in close proximity to the seedor plant to be protected from attack. The compound of the invention canbe washed into the soil by spraying with water over the area or can beleft to the natural action of rainfall. During or after application, theformulated compound can, if desired, be distributed mechanically in thesoil, for example by ploughing, disking, or use of drag chains.Application can be prior to planting, at planting, after planting butbefore sprouting has taken place, or after sprouting.

The compound of the invention and methods of control of pests therewithare of particular value in the protection of field, forage, plantation,glasshouse, orchard or vineyard crops, of ornamentals, or of plantationor forest trees, for example: cereals (such as wheat or rice), cotton,vegetables (such as peppers), field crops (such as sugar beets, soybeansor oil seed rape), grassland or forage crops (such as maize or sorghum),orchards or groves (such as of stone or pit fruit or citrus), ornamentalplants, flowers or vegetables or shrubs under glass or in gardens orparks, or forest trees (both deciduous and evergreen) in forests,plantations or nurseries.

They are also valuable in the protection of timber (standing, felled,converted, stored or structural) from attack, for example, by sawfliesor beetles or termites.

They have applications in the protection of stored products such asgrains, fruits, nuts, spices or tobacco, whether whole, milled orcompounded into products, from moth, beetle, mite or grain weevilattack. Also protected are stored animal products such as skins, hair,wool or feathers in natural or converted form (e.g. as carpets ortextiles) from moth or beetle attack as well as stored meat, fish orgrains from beetle, mite or fly attack.

Additionally, the compound of the invention and methods of use thereofare of particular value in the control of arthropods or helminths whichare injurious to, or spread or act as vectors of diseases domesticanimals, for example those hereinbefore mentioned, and more especiallyin the control of ticks, mites, lice, fleas, midges, or biting, nuisanceor myiasis flies. The compounds of the invention are particularly usefulin controlling arthropods or helminths which are present inside domestichost animals or which feed in or on the skin or suck the blood of theanimal, for which purpose they may be administered orally, parenterally,percutaneously or topically.

The compositions hereinafter described for application to growing cropsor crop growing loci or as a seed dressing may, in general,alternatively be employed in the protection of stored products,household goods, property or areas of the general environment. Suitablemeans of applying the compounds of the invention include: to growingcrops as foliar sprays (for example as an in-furrow spray), dusts,granules, fogs or foams or also as suspensions of finely divided orencapsulated compositions as soil or root treatments by liquid drenches,dusts, granules, smokes or foams; to seeds of crops via application asseed dressings by liquid slurries or dusts;

to animals infested by or exposed to infestation by arthropods orhelminths, by parenteral, oral or topical application of compositions inwhich the active ingredient exhibits an immediate and/or prolongedaction over a period of time against the arthropods or helminths, forexample by incorporation in feed or suitable orally-ingestiblepharmaceutical formulations, edible baits, salt licks, dietarysupplements, pour-on formulations, sprays, baths, dips, showers, jets,dusts, greases, shampoos, creams, wax smears or livestock self-treatmentsystems;to the environment in general or to specific locations where pests maylurk, including stored products, timber, household goods, or domestic orindustrial premises, as sprays, fogs, dusts, smokes, wax-smears,lacquers, granules or baits, or in tricklefeeds to waterways, wells,reservoirs or other running or standing water.

The compounds of the formula (I) can also be employed for controllingharmful organisms in crops of known genetically engineered plants orgenetically engineered plants yet to be developed. As a rule, thetransgenic plants are distinguished by especially advantageousproperties, for example by resistances to particular crop protectionagents, resistances to plant diseases or pathogens of plant diseases,such as particular insects or microorganisms such as fungi, bacteria orviruses. Other particular properties concern, for example, the harvestedmaterial with regard to quantity, quality, storage properties,composition and specific constituents. Thus, transgenic plants are knownwhere the starch content is increased, or the starch quality is altered,or where the harvested material has a different fatty acid composition.

The use in economically important transgenic crops of useful plants andornamentals is preferred, for example of cereals such as wheat, barley,rye, oats, millet, rice, cassava and maize or else crops of sugar beet,cotton, soya, oilseed rape, potatoes, tomatoes, peas and other types ofvegetables.

When used in transgenic crops, in particular those which haveresistances to insects, effects are frequently observed, in addition tothe effects against harmful organisms to be observed in other crops,which are specific for application in the transgenic crop in question,for example an altered or specifically widened spectrum of pests whichcan be controlled, or altered application rates which may be employedfor application.

The invention therefore also relates to the use of compounds of theformula (I) for controlling harmful organisms in transgenic crop plants.

According to a further feature of the present invention there isprovided a pesticidal composition comprising one or more compounds ofthe invention as defined above, in association with, and preferablyhomogeneously dispersed in one or more compatible pesticidallyacceptable diluents or carriers and/or surface active agents [i.e.diluents or carriers and/or surface active agents of the type generallyaccepted in the art as being suitable for use in pesticidal compositionsand which are compatible with compounds of the invention].

In practice, the compounds of the invention most frequently form partsof compositions. These compositions can be employed to controlarthropods, especially insects and acarids, or helminths such as plantnematodes. The compositions may be of any type known in the art suitablefor application to the desired pest in any premises or indoor or outdoorarea. These compositions contain at least one compound of the inventionas the active ingredient in combination or association with one or moreother compatible components which are for example, solid or liquidcarriers or diluents, adjuvants, surface-active-agents, or the likeappropriate for the intended use and which are agronomically ormedicinally acceptable. These compositions, which may be prepared by anymanner known in the art, likewise form a part of this invention.

The compounds of the invention, in their commercially availableformulations and in the use forms prepared from these formulations maybe present in mixtures with other active substances such asinsecticides, attractants, sterilants, acaricides, nematicides,fungicides, growth regulatory substances or herbicides.

The pesticides include, for example, phosphoric esters, carbamates,carboxylic esters, formamidines, tin compounds and materials produced bymicroorganisms. p Preferred components in mixtures are:

-   1. from the group of the phosphorus compounds    acephate, azamethiphos, azinphos-ethyl, azinphos-methyl, bromophos,    bromophos-ethyl, cadusafos (F-67825), chlorethoxyphos,    chlorfenvinphos, chlormephos, chlorpyrifos, chlorpyrifos-methyl,    demeton, demeton-S-methyl, demeton-S-methyl sulfone, dialifos,    diazinon, dichlorvos, dicrotophos, dimethoate, disulfoton, EPN,    ethion, ethoprophos, etrimfos, famphur, fenamiphos, fenitriothion,    fensulfothion, fenthion, flupyrazofos, fonofos, formothion,    fosthiazate, heptenophos, isazophos, isothioate, isoxathion,    malathion, methacrifos, methamidophos, methidathion, salithion,    mevinphos, monocrotophos, naled, omethoate, oxydemeton-methyl,    parathion, parathion-methyl, phenthoate, phorate, phosalone,    phosfolan, phosphocarb (BAS-301), phosmet, phosphamidon, phoxim,    pirimiphos, pirimiphos-ethyl, pirimiphos-methyl, profenofos,    propaphos, proetamphos, prothiofos, pyraclofos, pyridapenthion,    quinalphos, sulprofos, temephos, terbufos, tebupirimfos,    tetrachlorvinphos, thiometon, triazophos, trichlorphon, vamidothion;-   2. from the group of the carbamates    alanycarb (OK-135), aldicarb, 2-sec-butylphenyl methylcarbamate    (BPMC), carbaryl, carbofuran, carbosulfan, cloethocarb, benfuracarb,    ethiofencarb, furathiocarb, HCN-801, isoprocarb, methomyl,    5-methyl-m-cumenylbutyryl(methyl)carbamate, oxamyl, pirimicarb,    propoxur, thiodicarb, thiofanox,    1-methylthio(ethylideneamino)-N-methyl-N-(morpholinothio)carbamate    (UC 51717), triazamate;-   3. from the group of the carboxylic esters    acrinathrin, allethrin, alphametrin,    5-benzyl-3-furylmethyl(E)-(1R)-cis-2,2-dimethyl-3-(2-oxothiolan-3-ylidenemethyl)cyclopropanecarboxylate,    beta-cyfluthrin, alpha-cypermethrin, beta-cypermethrin,    bioallethrin, bioallethrin ((S)-cyclopentylisomer), bioresmethrin,    bifenthrin,    (RS)-1-cyano-1-(6-phenoxy-2-pyridyl)methyl(1RS)-trans-3-(4-tert-butylphenyl)-2,2-dimethylcyclopropanecarboxylate    (NCI 85193), cycloprothrin, cyfluthrin, cyhalothrin, cythithrin,    cypermethrin, cyphenothrin, deltamethrin, empenthrin, esfenvalerate,    fenfluthrin, fenpropathrin, fenvalerate, flucythrinate, flumethrin,    fluvalinate (D isomer), imiprothrin (S-41311), lambda-cyhalothrin,    permethrin, phenothrin (® isomer), prallethrin, pyrethrins (natural    products), resmethrin, tefluthrin, tetramethrin, theta-cypermethrin,    tralomethrin, transfluthrin, zeta-cypermethrin (F-56701);-   4. from the group of the amidines    amitraz, chlordimeform;-   5. from the group of the tin compounds    cyhexatin, fenbutatin oxide;-   6. others    abamectin, ABG-9008, acetamiprid, acequinocyl, Anagrapha falcitera,    AKD-1022, AKD-3059, ANS-118, azadirachtin, Bacillus thuringiensis,    Beauveria bassianea, bensultap, bifenazate, binapacryl, BJL-932,    bromopropylate, BTG-504, BTG-505, buprofezin, camphechlor, cartap,    chlorobenzilate, chlorfenapyr, chlorfluazuron,    2-(4-chlorophenyl)-4,5-diphenylthiophene (UBI-T 930),    chlorfentezine, chlorproxyfen, chromafenozide, clothianidine,    2-naphthylmethyl cyclopropanecarboxylate (Ro12-0470), cyromazin,    diacloden (thiamethoxam), diafenthiuron, DBI-3204, ethyl    2-chloro-N-(3,5-dichloro-4-(1,1,2,3,3,3-hexafluoro-1-propyloxy)phenyl)carbamoyl)-2-carboximidate,    DDT, dicofol, diflubenzuron,    N-(2,3-dihydro-3-methyl-1,3-thiazol-2-ylidene)-2,4-xylidine,    dihydroxymethyldihydroxypyrrolidine, dinobuton, dinocap, diofenolan,    emamectin benzoate, endosulfan, ethiprole (sulfethiprole),    ethofenprox, etoxazole, fenazaquin, fenoxycarb, fipronil, fluazuron,    flumite (flufenzine, SZI-121),    2-fluoro-5-(4-(4-ethoxyphenyl)-4-methyl-1-pentyl)diphenyl ether (MTI    800), granulosis and nuclear polyhedrosis viruses, fenpyroximate,    fenthiocarb, fluacrypyrim, flubenzimine, flubrocythrinate,    flucycloxuron, flufenoxuron, flufenzine, flufenprox, fluproxyfen,    gamma-HCH, halfenozide, halofenprox, hexaflumuron (DE_(—)473),    hexythiazox, HOI-9004, hydramethylnon (AC 217300), IKI-220,    indoxacarb, ivermectin, L-14165, imidacloprid, indoxacarb    (DPX-MP062), kanemite (AKD-2023), lufenuron, M-020, M-020,    methoxyfenozide, milbemectin, NC-196, neemgard, nidinoterfuran,    nitenpyram, 2-nitromethyl-4,5-dihydro-6H-thiazine (DS 52618),    2-nitromethyl-3,4-dihydrothiazole (SD 35651),    2-nitromethylene-1,2-thiazinan-3-ylcarbamaldehyde (WL 108477),    novaluron, pirydaryl, propargite, protrifenbute, pymethrozine,    pyridaben, pyrimidifen, pyriproxyfen, NC-196, NC-1111, NNI-9768,    novaluron (MCW-275), OK-9701, OK-9601, OK-9602, OK-9802, R-195,    RH-0345, RH-2485, RYI-210, S-1283, S-1833, SI-8601, silafluofen,    silomadine (CG-177), spinosad, spirodiclofen, SU-9118, tebufenozide,    tebufenpyrad, teflubenzuron, tetradifon, tetrasul, thiacloprid,    thiocyclam, thiamethoxam, tolfenpyrad, triazamate, triethoxyspinosyn    A, triflumuron, verbutin, vertalec (mykotal), YI-5301.

The abovementioned components for combinations are known activesubstances, many of which are described in Ch. R Worthing, S. B. Walker,The Pesticide Manual, 12^(th) Edition, British Crop Protection Council,Farnham 2000.

The effective use doses of the compounds employed in the invention canvary within wide limits, particularly depending on the nature of thepest to be eliminated or degree of infestation, for example, of cropswith these pests. In general, the compositions according to theinvention usually contain about 0.05 to about 95% (by weight) of one ormore active ingredients according to the invention, about 1 to about 95%of one or more solid or liquid carriers and, optionally, about 0.1 toabout 50% of one or more other compatible components, such assurface-active agents or the like. In the present account, the term“carrier” denotes an organic or inorganic ingredient, natural orsynthetic, with which the active ingredient is combined to facilitateits application, for example, to the plant, to seeds or to the soil.This carrier is therefore generally inert and it must be acceptable (forexample, agronomically acceptable, particularly to the treated plant).

The carrier may be a solid, for example, clays, natural or syntheticsilicates, silica, resins, waxes, solid fertilizers (for exampleammonium salts), ground natural minerals, such as kaolins, clays, talc,chalk, quartz, attapulgite, montmorillonite, bentonite or diatomaceousearth, or ground synthetic minerals, such as silica, alumina, orsilicates especially aluminium or magnesium silicates. As solid carriersfor granules the following are suitable: crushed or fractionated naturalrocks such as calcite, marble, pumice, sepiolite and dolomite; syntheticgranules of inorganic or organic meals; granules of organic materialsuch as sawdust, coconut shells, corn cobs, corn husks or tobaccostalks; kieselguhr, tricalcium phosphate, powdered cork, or absorbentcarbon black; water soluble polymers, resins, waxes; or solidfertilizers. Such solid compositions may, if desired, contain one ormore compatible wetting, dispersing, emulsifying or colouring agentswhich, when solid, may also serve as a diluent.

The carrier may also be liquid, for example: water; alcohols,particularly butanol or glycol, as well as their ethers or esters,particularly methylglycol acetate; ketones, particularly acetone,cyclohexanone, methylethyl ketone, methylisobutylketone, or isophorone;petroleum fractions such as paraffinic or aromatic hydrocarbons,particularly xylenes or alkyl naphthalenes; mineral or vegetable oils;aliphatic chlorinated hydrocarbons, particularly trichloroethane ormethylene chloride; aromatic chlorinated hydrocarbons, particularlychlorobenzenes; water-soluble or strongly polar solvents such asdimethylformamide, dimethyl sulphoxide, or N-methylpyrrolidone;liquefied gases; or the like or a mixture thereof.

The surface-active agent may be an emulsifying agent, dispersing agentor wetting agent of the ionic or non-ionic type or a mixture of suchsurface-active agents. Amongst these are e.g., salts of polyacrylicacids, salts of lignosulphonic acids, salts of phenolsulphonic ornaphthalenesulphonic acids, polycondensates of ethylene oxide with fattyalcohols or fatty acids or fatty esters or fatty amines, substitutedphenols (particularly alkylphenols or arylphenols), salts ofsulphosuccinic acid esters, taurine derivatives (particularlyalkyltaurates), phosphoric esters of alcohols or of polycondensates ofethylene oxide with phenols, esters of fatty acids with polyols, orsulphate, sulphonate or phosphate functional derivatives of the abovecompounds. The presence of at least one surface-active agent isgenerally essential when the active ingredient and/or the inert carrierare only slightly water soluble or are not water soluble and the carrieragent of the composition for application is water. Compositions of theinvention may further contain other additives such as adhesives orcolorants. Adhesives such as carboxymethylcellulose or natural orsynthetic polymers in the form of powders, granules or lattices, such asarabic gum, polyvinyl alcohol or polyvinyl acetate, naturalphospholipids, such as cephalins or lecithins, or syntheticphospholipids can be used in the formulations. It is possible to usecolorants such as inorganic pigments, for example: iron oxides, titaniumoxides or Prussian Blue; organic dyestuffs, such as alizarin dyestuffs,azo dyestuffs or metal phthalocyanine dyestuffs; or trace nutrients suchas salts of iron, manganese, boron, copper, cobalt, molybdenum or zinc.

For their agricultural application, the compounds of the invention aretherefore generally in the form of compositions, which are in varioussolid or liquid forms. Solid forms of compositions which can be used aredusting powders (with a content of the compound of the invention,ranging up to 80%), wettable powders or granules (including waterdispersible granules), particularly those obtained by extrusion,compacting, impregnation of a granular carrier, or granulation startingfrom a powder (the content of the compound of the invention, in thesewettable powders or granules being between about 0.5 and about 80%).Solid homogenous or heterogenous compositions containing one or morecompounds of the invention, for example granules, pellets, briquettes orcapsules, may be used to treat standing or running water over a periodof time. A similar effect may be achieved using trickle or intermittentfeeds of water dispersible concentrates as described herein.

Liquid compositions, for example, include aqueous or non-aqueoussolutions or suspensions (such as emulsifiable concentrates, emulsions,flowables, dispersions, or solutions) or aerosols. Liquid compositionsalso include, in particular, emulsifiable concentrates, dispersions,emulsions, flowables, aerosols, wettable powders (or powder forspraying), dry flowables or pastes as forms of compositions which areliquid or intended to form liquid compositions when applied, for exampleas aqueous sprays (including low and ultra-low volume) or as fogs oraerosols.

Liquid compositions, for example, in the form of emulsifiable or solubleconcentrates most frequently comprise about 5 to about 80% by weight ofthe active ingredient, while the emulsions or solutions which are readyfor application contain, in their case, about 0.01 to about 20% of theactive ingredient. Besides the solvent, the emulsifiable or solubleconcentrates may contain, when required, about 2 to about 50% ofsuitable additives, such as stabilizers, surface-active agents,penetrating agents, corrosion inhibitors, colorants or adhesives.Emulsions of any required concentration, which are particularly suitablefor application, for example, to plants, may be obtained from theseconcentrates by dilution with water. These compositions are includedwithin the scope of the compositions which may be employed in thepresent invention. The emulsions may be in the form of water-in-oil oroil-in-water type and they may have a thick consistency.

The liquid compositions of this invention may, in addition to normalagricultural use applications be used for example to treat substrates orsites infested or liable to infestation by arthropods (or other pestscontrolled by compounds of this invention) including premises, outdooror indoor storage or processing areas, containers or equipment orstanding or running water.

All these aqueous dispersions or emulsions or spraying mixtures can beapplied, for example, to crops by any suitable means, chiefly byspraying, at rates which are generally of the order of about 100 toabout 1,200 liters of spraying mixture per hectare, but may be higher orlower (eg. low or ultra-low volume) depending upon the need orapplication technique. The compound or compositions according to theinvention are conveniently applied to vegetation and in particular toroots or leaves having pests to be eliminated. Another method ofapplication of the compounds or compositions according to the inventionis by chemigation, that is to say, the addition of a formulationcontaining the active ingredient to irrigation water. This irrigationmay be sprinkler irrigation for foliar pesticides or it can be groundirrigation or underground irrigation for soil or for systemicpesticides.

The concentrated suspensions, which can be applied by spraying, areprepared so as to produce a stable fluid product which does not settle(fine grinding) and usually contain from about 10 to about 75% by weightof active ingredient, from about 0.5 to about 30% of surface-activeagents, from about 0.1 to about 10% of thixotropic agents, from about 0to about 30% of suitable additives, such as anti-foaming agents,corrosion inhibitors, stabilizers, penetrating agents, adhesives and, asthe carrier, water or an organic liquid in which the active ingredientis poorly soluble or insoluble Some organic solids or inorganic saltsmay be dissolved in the carrier to help prevent settling or asantifreezes for water.

The wettable powers (or powder for spraying) are usually prepared sothat they contain from about 10 to about 80% by weight of activeingredient, from about 20 to about 90% of a solid carrier, from about 0to about 5% of a wetting agent, from about 3 to about 10% of adispersing agent and, when necessary, from about 0 to about 80% of oneor more stabilizers and/or other additives, such as penetrating agents,adhesives, anti-caking agents, colorants, or the like. To obtain thesewettable powders, the active ingredient is thoroughly mixed in asuitable blender with additional substances which may be impregnated onthe porous filler and is ground using a mill or other suitable grinder.This produces wettable powders, the wettability and the suspendabilityof which are advantageous. They may be suspended in water to give anydesired concentration and this suspension can be employed veryadvantageously in particular for application to plant foliage.

The “water dispersible granules (WG)” (granules which are readilydispersible in water) have compositions which are substantially close tothat of the wettable powders. They may be prepared by granulation offormulations described for the wettable powders, either by a wet route(contacting finely divided active ingredient with the inert filler and alittle water, e.g. 1 to 20% by weight, or with an aqueous solution of adispersing agent or binder, followed by drying and screening), or by adry route (compacting followed by grinding and screening).

The rates and concentrations of the formulated compositions may varyaccording to the method of application or the nature of the compositionsor use thereof. Generally speaking, the compositions for application tocontrol arthropod or helminth pests usually contain from about 0.00001%to about 95%, more particularly from about 0.0005% to about 50% byweight of one or more compounds of the invention, or of total activeingredients (that is to say the compounds of the invention, togetherwith other substances toxic to arthropods or helminths, synergists,trace elements or stabilizers). The actual compositions employed andtheir rate of application will be selected to achieve the desiredeffect(s) by the farmer, livestock producer, medical or veterinarypractitioner, pest control operator or other person skilled in the art.Solid or liquid compositions for application topically to animals,timber, stored products or household goods usually contain from about0.00005% to about 90%, more particularly from about 0.001% to about 10%,by weight of one or more compounds of the invention. For administrationto animals orally or parenterally, including percutaneously solid orliquid compositions, these normally contain from about 0.1% to about 90%by weight of one or more compounds of the invention. Medicatedfeedstuffs normally contain from about 0.001% to about 3% by weight ofone or more compounds of the invention. Concentrates or supplements formixing with feedstuffs normally contain from about 5% to about 90%,preferably from about 5% to about 50%, by weight of one or morecompounds of the invention. Mineral salt licks normally contain fromabout 0.1% to about 10% by weight of one or more compounds of formula(I) or pesticidally acceptable salts thereof.

Dusts or liquid compositions for application to livestock, goods,premises or outdoor areas may contain from about 0.0001% to about 15%,more especially from about 0.005% to about 2.0%, by weight, of one ormore compounds of the invention. Suitable concentrations in treatedwaters are between about 0.0001 ppm and about 20 ppm, more particularlyabout 0.001 ppm to about 5.0 ppm. of one or more compounds of theinvention, and may be used therapeutically in fish farming withappropriate exposure times. Edible baits may contain from about 0.01% toabout 5%, preferably from about 0.01% to about 1.0%, by weight, of oneor more compounds of the invention.

When administered to vertebrates parenterally, orally or by percutaneousor other means, the dosage of compounds of the invention, will dependupon the species, age, or health of the vertebrate and upon the natureand degree of its actual or potential infestation by arthropod orhelminth pests. A single dose of about 0.1 to about 100 mg, preferablyabout 2.0 to about 20.0 mg, per kg body weight of the animal or doses ofabout 0.01 to about 20.0 mg, preferably about 0.1 to about 5.0 mg, perkg body weight of the animal per day, for sustained medication, aregenerally suitable by oral or parenteral administration. By use ofsustained release formulations or devices, the daily doses required overa period of months may be combined and administered to animals on asingle occasion.

The following composition EXAMPLES 2A-2M illustrate compositions for useagainst arthropods, especially insects or acarids, or helminths such asplant nematodes, which comprise, as active ingredient, compounds of theinvention, such as those described in preparative examples. Thecompositions described in EXAMPLES 2A-2M can each be diluted to give asprayable compositon at concentrations suitable for use in the field.Generic chemical descriptions of the ingredients (for which all of thefollowing percentages are in weight percent), used in the compositionEXAMPLES 2A-2M exemplified below, are as follows:

Trade Name Chemical Description Ethylan BCP Nonylphenol ethylene oxidecondensate Soprophor BSU Tristyrylphenol ethylene oxide condensateArylan CA A 70% w/v solution of calcium dodecylbenzenesulfonate Solvesso150 Light C₁₀ aromatic solvent Arylan S Sodium dodecylbenzenesulfonateDarvan NO₂ Sodium lignosulphonate Celite PF Synthetic magnesium silicatecarrier Sopropon T36 Sodium salts of polycarboxylic acids Rhodigel 23Polysaccharide xanthan gum Bentone 38 Organic derivative of magnesiummontmorillonite Aerosil Microfine silicon dioxide

Example 2A

A water soluble concentrate is prepared with the composition as follows:

Active ingredient 7% Ethylan BCP 10% N-methylpyrrolidone 83%

To a solution of Ethylan BCP dissolved in a portion ofN-methylpyrrolidone is added the active ingredient with heating andstirring until dissolved. The resulting solution is made up to volumewith the remainder of the solvent.

Example 2B

An emulsifiable concentrate (EC) is prepared with the composition asfollows:

Active ingredient 25% (max) Soprophor BSU 10% Arylan CA  5%N-methylpyrrolidone 50% Solvesso 150 10%

The first three components are dissolved in N-methylpyrrolidone and tothis is then added the Solvesso 150 to give the final volume.

Example 2C

A wettable powder (WP) is prepared with the composition as follows:

Active ingredient 40% Arylan S 2% Darvan NO₂ 5% Celite PF 53%

The ingredients are mixed and ground in a hammer-mill to a powder with aparticle size of less than 50 microns.

Example 2D

An aqueous-flowable formulation is prepared with the composition asfollows:

Active ingredient 40.00% Ethylan BCP 1.00% Sopropon T360. 0.20% Ethyleneglycol 5.00% Rhodigel 230. 0.15% Water 53.65%

The ingredients are intimately mixed and are ground in a bead mill untila mean particle size of less than 3 microns is obtained.

Example 2E

An emulsifiable suspension concentrate is prepared with the compositionas follows:

Active ingredient 30.0% Ethylan BCP 10.0% Bentone 38 0.5% Solvesso 15059.5%

The ingredients are intimately mixed and ground in a beadmill until amean particle size of less than 3 microns is obtained.

Example 2F

A water dispersible granule is prepared with the composition as follows:

Active ingredient 30% Darvan No 2 15% Arylan S 8% Celite PF 47%

The ingredients are mixed, micronized in a fluid-energy mill and thengranulated in a rotating pelletizer by spraying with water (up to 10%).The resulting granules are dried in a fluid-bed drier to remove excesswater.

Example 2G

A dusting powder is prepared with the composition as follows:

Active ingredient  1 to 10% Talc powder-superfine 99 to 90%

The ingredients are intimately mixed and further ground as necessary toachieve a fine powder. This powder may be applied to a locus ofarthropod infestation, for example refuse dumps, stored products orhousehold goods or animals infested by, or at risk of infestation by,arthropods to control the arthropods by oral ingestion. Suitable meansfor distributing the dusting powder to the locus of arthropodinfestation include mechanical blowers, handshakers or livestock selftreatment devices.

Example 2H

An edible bait is prepared with the composition as follows:

Active ingredient 0.1 to 1.0% Wheat flour 80% Molasses 19.9 to 19%  

The ingredients are intimately mixed and formed as required into a baitform. This edible bait may be distributed at a locus, for exampledomestic or industrial premises, e.g. kitchens, hospitals or stores, oroutdoor areas, infested by arthropods, for example ants, locusts,cockroaches or flies, to control the arthropods by oral ingestion.

Example 2I

A solution formulation is prepared with a composition as follows:

Active ingredient 15% Dimethyl sulfoxide 85%

The active ingredient is dissolved in dimethyl sulfoxide with mixing andor heating as required. This solution may be applied percutaneously as apour-on application to domestic animals infested by arthropods or, aftersterilization by filtration through a polytetrafluoroethylene membrane(0.22 micrometer pore size), by parenteral injection, at a rate ofapplication of from 1.2 to 12 ml of solution per 100 kg of animal bodyweight.

Example 2J

A wettable powder is prepared with the composition as follows:

Active ingredient 50% Ethylan BCP 5% Aerosil 5% Celite PF 40%

The Ethylan BCP is absorbed onto the Aerosil which is then mixed withthe other ingredients and ground in a hammer-mill to give a wettablepowder, which may be diluted with water to a concentration of from0.001% to 2% by weight of the active compound and applied to a locus ofinfestation by arthropods, for example, dipterous larvae or plantnematodes, by spraying, or to domestic animals infested by, or at riskof infection by arthropods, by spraying or dipping, or by oraladministration in drinking water, to control the arthropods.

Example 2K

A slow release bolus composition is formed from granules containing thefollowing components in varying percentages (similar to those describedfor the previous compositions) depending upon need:

Active ingredient Density agent Slow-release agent Binder

The intimately mixed ingredients are formed into granules which arecompressed into a bolus with a specific gravity of 2 or more. This canbe administered orally to ruminant domestic animals for retention withinthe reticulo-rumen to give a continual slow release of active compoundover an extended period of time to control infestation of the ruminantdomestic animals by arthropods.

Example 2L

A slow release composition in the form of granules, pellets, brickettesor the like can be prepared with compositions as follows:

Active ingredient 0.5 to 25% Polyvinyl chloride  75 to 99.5% Dioctylphthalate (plasticizer)

The components are blended and then formed into suitable shapes bymelt-extrusion or molding. These composition are useful, for example,for addition to standing water or for fabrication into collars oreartags for attachment to domestic animals to control pests by slowrelease.

Example 2M

A water dispersible granule is prepared with the composition as follows:

Active ingredient 85%(max) Polyvinylpyrrolidone  5% Attapulgite clay  6%Sodium lauryl sulfate  2% Glycerine  2%

The ingredients are mixed as a 45% slurry with water and wet milled to aparticle size of 4 microns, then spray-dried to remove water.

Methods of Pesticidal use

The following representative test procedures, using compounds of theinvention, were conducted to determine the parasiticidal and pesticidalactivity of compounds of the invention.

Method A:

Germinated field bean seeds (Vicia faba) with seed roots weretransferred into brown glass bottles filled with tap water and thenpopulated with about 100 black bean aphids (Aphis fabae). Plants andaphids were then dipped into an aqueous solution of the formulatedpreparation to be examined for 5 seconds. After they had drained, plantsand animals were stored in a climatized chamber (16 hours of light/day,25° C., 40-60% relative atmospheric humidity). After 3 and 6 days ofstorage, the effect of the preparation on the aphids was determined. Ata concentration of 100 ppm (based on the content of active compound),the following Compounds caused a mortality of at least 50% among theaphids:

A-18, A-64, A-65, A-71, A-74, A-79, A-81, A-86, A-88, A-206, A-209,A-223, A-255, A-261, A-262, A-265, A-267, A-268, A-292, A-296, A-312,A-312, A-316, A-317, A-326, A-329, A-349, A-353, A-354, A-355, A-365,A-366, A-367, A-369, A-373, A-381, A-398, A-431, A-524, A-529, A-540,A-544, A-564, A-605, A-626, A-691, A-697, A-713, A-736, A-737, A-738,A-744, A-745, A-747, A-748, A-798, A-799, A-805, A-822, A-861, A-862,A-865, A-867, A-874, B-37, B-40, B-47, B-65, B-74, B-149, B-150, B-151,B-152, B-155, B-158, B-163, B-166, B-167, B-168, B-169, B-170, B-176,B-184, B-185, B-189, B-247, B-251, B-255, B-258, B-259, B-261, B-267,B-269, B-296, B-313, B-349, B-353, B-354, B-355, B-366, B-369, B-373,B-398, B-431, B-564, B-713, B-736, B-737, B-738, B-744, B-745, B-747,B748, B-799, B-805, B-822, B-861, B-863, B-864, B-865, B-867, B-869,B-870, B-871, B-873, B-874, B-877, C-85, E-85, F-85, F-88, H-85, S-548,S-550, S-551, S-552, S-553, S-555, S-556, S-558, S-559, U-3, U-7, U-20,X-45 and X-55.Method B:

Germinated field bean seeds (Vicia faba) with seed roots weretransferred into brown glass bottles filled with tap water. Fourmilliliters of an aqueous solution of the formulated preparation to beexamined were pipetted into the brown glass bottle. The field bean wasthen heavily populated with about 100 black bean aphids (Aphis fabae).Plants and aphids were then stored in a climatized chamber (16 hours oflight/day, 25° C., 40-60% relative atmospheric humidity). After 3 and 6days of storage, the root-systemic effect of the preparation on theaphids was determined. At a concentration of 10 ppm (based on thecontent of active compound), the following Compounds caused a mortalityof at least 80% among the aphids, by root-systemic action:

A-39, A-64, A-65, A-67, A-71, A-74, A-79, A-81, A-86, A-88, A-89, A-90,A-209, A-212, A-223, A-262, A-265, A-267, A-268, A-292, A-296, A-313,A-317, A-326, A-329, A-349, A-354, A-355, A-365, A-366, A-367, A-369,A-373, A-381, A-398, A-431, A-519, A-524, A-529, A-540, A-544, A-564,A-605, A-626, A-691, A-697, A-713, A-736, A-737, A-738, A-744, A-745,A-747, A-748, A-798, A-799, A-805, A-822, A-861, A-862, A-865, A-867,A-871, A-873, A-874, B-37, B-40, B-47, B-65, B-71, B-74, B-86, B-149,B-150, B-151, B-152, B-155, B-158, B-166, B-167, B-169, B-170, B-176,B-184, B-189, B-247, B-251, B-255, B-257, B-258, B-259, B-261, B-267,B-269, B-296, B-313, B-349, B-353, B-354, B-355, B-366, B-369, B-373,B-398, B-564, B-713, B-736, B-737, B-738, B-744, B-745, B-748, B-799,B-805, B-861, B-863, B-864, B-865, B-867, B-869, B-870, B-871, B-872,B-873, B-874, B-877, C-85, D-86, E-85, F-85, F-88, G-85, H-85, S-3,S-120, S-356, S-548, S-550, S-551, S-553, S-556, S-557, S-558, S-559,U-3, U-7, U-20, X-45 and X-55.

1. A compound of the formula (I):

wherein: R¹ is —C(═U)NR³R⁴; R² is H, (C₁-C₆)alkyl or R³; R³ is R⁵, OH orNH₂; or is (C₁-C₆)alkyl substituted by one or more R⁶ groups; R⁴ is H orR⁵; or is (C₁-C₆)alkyl unsubstituted or substituted by one or more R⁶groups; R⁵ is (C₃-C₆)alkenyl, (C₃-C₆)alkynyl, (C₃-C₈)cycloalkyl,(C₁-C₆)alkoxy, (C₃-C₆)alkenyloxy, (C₃-C₆)alkynyloxy, (C₁-C₆)alkylamino,di-(C₁-C₆)alkylamino, CO(C₁-C₆)alkyl, NHCO(C₁-C₆)alkyl,NHSO₂(C₁-C₆)alkyl or SO₂(C₁-C₆)alkyl which last 12 mentioned groups areunsubstituted or substituted by one or more R⁶ groups; or is(C₃-C₈)cycloalkyl-(C₁-C₆)alkyl which cycloalkyl group is unsubstitutedor substituted by one or more R⁶ groups; or is NH(CHR¹⁴)_(s)aryl,—(CR¹⁵R¹⁶)_(p)aryl, O(R¹⁵R¹⁶)_(r)aryl, NHCOaryl, CO(CH₂)_(t)aryl,NHSO₂aryl, SO₂(CH₂)_(u)aryl or N═C(aryl)₂, which aryl groups areunsubstituted or substituted by one or more R¹⁷ groups; or isO(CR¹⁵R¹⁶)_(p)(C₃-C₈)cycloalkyl or N═C[(C₁-C₆)alkyl]₂; R⁶ is halogen,(C₁-C₆)alkoxy, (C₁-C₆)haloalkoxy, S(O)_(n)R^(14a), CN, CO₂(C₁-C₆)alkyl,CO₂H, NO₂, OH, amino, (C₁-C₆)alkylamino, di-(C₁-C₆)alkylamino,carbamoyl, (C₁-C₆)-alkylcarbamoyl, di-(C₁-C₆)-alkylcarbamoyl orCH[O(C₁-C₆)alkyl]₂; or is phenoxy unsubstituted or substituted by one ormore R^(14a) or halogen groups; R¹⁷ is R⁶, R^(14a) or CH₂OH; U is S orO; R¹⁴, R¹⁵ and R¹⁶ are each independently H, (C₁-C₆)alkyl or(C₁-C₆)haloalkyl; R^(14a) is (C₁-C₆)alkyl or (C₁-C₆)haloalkyl; m is zeroor one; n, p, r, s, t and u are each independently zero, one or two; qis one, two or three; or a pesticidally acceptable salt thereof; withthe exclusion of the compound wherein R¹ is —C(═U)NR³R⁴; U is O; R² isH; m is zero; R⁴ is H and R³ is 2,4-dichlorophenyl.
 2. A compound or asalt thereof as claimed in claim 1, wherein R² is H or R³.
 3. A compoundor a salt thereof as claimed in claim 1, wherein R³ is R⁵ or OH; or is(C₁-C₆)alkyl substituted by one or more R⁶ groups.
 4. A compound or asalt thereof as claimed in claim 1, wherein R² is H; R³ is R⁵ or OH; oris (C₁-C₆)alkyl substituted by one or more R⁶ groups; R⁴ is H or R⁵, oris (C₁-C₆)alkyl unsubstituted or substituted by one or more R⁶ groups;R⁵ is (C₃-C₆)alkenyl, (C₃-C₆)alkynyl, (C₃-C₈)cycloalkyl,(C₃-C₈)cycloalkyl-(C₁-C₆)alkyl, (C₁-C₆)alkoxy, (C₃-C₆)alkenyloxy,(C₃-C₆)alkynyloxy or O(CR¹⁵R¹⁶)_(p)(C₃-C₈)cycloalkyl; or—(CR¹⁵R¹⁶)_(p)phenyl, O(CR¹⁵R¹⁶)_(r)phenyl which phenyl groups areunsubstituted or substituted by one or more R¹⁷ groups; R⁶ is halogen,(C₁-C₆)alkoxy, (C₁-C₆)haloalkoxy, S(O)_(n)R^(14a), CN, NO₂ or OH; R¹⁷ isR⁶, R^(14a) or CH₂OH; U is S or O; R¹⁴, R¹⁵ and R¹⁶ are each H or(C₁-C₆)alkyl; R^(14a) is (C₁-C₆)alkyl or (C₁-C₆)haloalkyl; m is zero; n,r, s, t and u are zero, one or two; q is one.
 5. A compound or a saltthereof as claimed in claim 1, wherein R² is H; U is O or S; R³ is(C₁-C₆)alkoxy, C₁-C₆)haloalkoxy, (C₃-C₆)alkenyloxy, (C₃-C₆)alkynyloxy,CH₂phenyl or OCH₂phenyl, or phenyl, which phenyl groups areunsubstituted or substituted by one or more groups selected fromhalogen, (C₁-C₆)alkyl, (C₁-C₆)alkoxy, CN and NO₂; R⁴ is H, (C₁-C₆)alkyl,(C₃-C₆)alkenyl, (C₃-C₆)alkynyl or CH₂phenyl; and m is zero.
 6. A processfor the preparation of a compound of formula (I) or a salt thereof asdefined in claim 1, which process comprises:

where R¹ is —C(═U)NR³R⁴, m is zero, R² is H, U is O, and R³ and R⁴ areas defined in formula (I), reacting a compound of formula (IX):

with oxalyl chloride or triphosgene, to give the correspondingacylisocyanate intermediate followed by reacting the resultantintermediate with an amine of formula (X):HNR³R⁴  (X) wherein R³ and R⁴ are as defined in formula (I); or ifdesired, converting a resulting compound of formula (I) into apesticidally acceptable salt thereof.
 7. A pesticidal compositioncomprising a pesticidally effective amount of a compound of formula (I)or a pesticidally acceptable salt thereof as defined in claim 1, inassociation with a pesticidally acceptable diluent or carrier and/orsurface active agent.
 8. A method for the control of arthropod ornematode pests, said method comprising applying to said pests or to alocus at which they reside or feed or which is susceptible toinfestation thereby, a pesticidally effective amount of a compound orsalt thereof as claimed in claim
 1. 9. A method for the control ofarthropod or nematode pests, said method comprising applying to saidpests or to a locus at which they reside or feed or which is susceptibleto infestation thereby, a pesticidally effective amount of a compositionas claimed in claim 7.